A Concise Account of Recent SN2′ Grignard Coupling Reactions in Organic Synthesis

Anirban Kar; Narshinha P. Argade

doi:10.1055/s-2005-918455

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Synthesis 2005(18): 2995-3022
DOI: 10.1055/s-2005-918455

REVIEW

A Concise Account of Recent S_N2′ Grignard Coupling Reactions in Organic Synthesis [1]

Anirban Kar*, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25893153; e-Mail: np.argade@ncl.res.in;

Further Information

Publication History

Received 19 May 2005
Publication Date:
28 October 2005 (online)

Abstract
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Abstract

Over the past few decades studies on controlling the chemo-, regio- and stereoselectivities of allylic substitution reactions have been well documented in the literature and the S_N2′ Grignard coupling reaction has emerged as a very powerful tool in selective carbon-carbon bond formation. This review focuses on all the recent synthetic developments in this special class of reactions.

1 Introduction
2 S_N2′ Grignard Coupling Reactions with Allylic Substrates
2.1 Allyl Halides
2.2 Allyl Acetates
2.3 Allyl Carbonates
2.4 Allyl Carbamates
2.5 Allyl Ethers
2.6 Allyl Silyl Ethers
2.7 Allyl Epoxides
2.8 Allyl Aziridines
2.9 Allyl Oxazolidinones
2.10 Allyl Thioethers
2.11 Allyl Benzotriazoles
2.12 Oxabicyclic Alkenes
2.13 Azabicyclic Alkenes
2.14 Oxa-azabicyclic Alkenes
3 S_N2′ Grignard Coupling Reactions with Propargyl Substrates
3.1 Propargyl Acetates
3.2 Propargyl Silyl Ethers
3.3 Propargyl Epoxides
3.4 Propargyl Aziridines
3.5 Propargyl Dithioacetals
3.6 Propargyl Thioethers
4 S_N2′ Grignard Coupling Reactions with Bromoallenes
5 S_N2′ Grignard Coupling Reactions in Natural/Unnatural Product Synthesis
6 Conclusions

Key words

chiral/achiral S_N2′ Grignard coupling reactions - allylic substrates - propargyl substrates - bromoallenes - natural products

1

NCL Communication No. 6683.

References

2 Barbier P. C. R. Hebd. Seances Acad. Sci. 1899, 128: 110

Google Scholar
3 Grignard VCR. C. R. Hebd. Seances Acad. Sci. 1900, 130: 1322

Google Scholar
4 Liotta CL. Tetrahedron Lett. 1975, 523

Crossref Google Scholar
5 Stohrer WD. Angew. Chem., Int. Ed. Engl. 1983, 22: 613

Crossref Google Scholar
6 Kharash MS. Reinmuth O. Grignard Reactions of Nonmetallic Substances Prentice-Hall; Englewood Cliffs, NJ: 1954.

Google Scholar
7a Silverman GS. Rakita PE. Handbook of Grignard Reagents, 1^st ed. Marcel Dekker; New York: 1996.

Google Scholar
7b Lipshutz BH. Sengupta S. In Organic Reactions, Vol. 41 Paquette LA. Wiley; New York: 1992. p.135

Google Scholar
8 Richey HG. Grignard Reagents - New Developments Wiley; Chichester: 2000.

Google Scholar
9 Normant JF. New Application of Organomatallic Reagents in Organic Synthesis Seyfert D. Elsevier; Amsterdam: 1976. p.219

Google Scholar
10 Posner GH. An Introduction to Synthesis Using Organocopper Reagents John Wiley & Sons; New York: 1980.

Google Scholar
11 Klunder JM. Posner GH. Comprehensive Organic Synthesis, Vol. 3 Trost BM. Fleming I. Pattenden G. Pergamon Press; Oxford: 1991. p.220

Google Scholar
12 Alexakis A. Malan C. Lea L. Benhaim C. Fournioux X. Synlett 2001, 927

Article in Thieme Connect Google Scholar
13 Alexakis A. Croset K. Org. Lett. 2002, 4: 4147

Crossref Google Scholar
14 Croset K.-T. Polet D. Alexakis A. Angew. Chem. Int. Ed. 2004, 43: 2426

Crossref PubMed Google Scholar
15 Yamazaki T. Umetani H. Kitazume T. Tetrahedron Lett. 1997, 38: 6705

Crossref Google Scholar
16 Kimura M. Yamazaki T. Kitazume T. Kubota T. Org. Lett. 2004, 6: 4651

Crossref Google Scholar
17 Kobayashi Y. Ito M. Igarashi J. Tetrahedron Lett. 2002, 43: 4829

Crossref Google Scholar
18a Chong JM. Belelie JL. J. Org. Chem. 2002, 67: 3000

Crossref Google Scholar
18b Arai M. Kawasujji T. Nakamura E. J. Org. Chem. 1993, 58: 5121

Crossref Google Scholar
19 Persson ESM. van Klaveren M. Grove DM. Bäckvall J.-E. van Koten G. Chem. Eur. J. 1995, 1: 351

Google Scholar
20 van Klaveren M. Persson ESM. del Villar A. Grove DM. Bäckvall J.-E. van Koten G. Tetrahedron Lett. 1995, 36: 3059

Crossref Google Scholar
21 Meuzelaar GJ. Karlström ASE. van Klaveren M. Persson ESM. del Villar A. van Koten G. Bäckvall J.-E. Tetrahedron 2000, 56: 2895

Crossref Google Scholar
22 Karlström ASE. Huerta FF. Meuzelaar GJ. Bäckvall J.-E. Synlett 2001, 923

Article in Thieme Connect Google Scholar
23 Spino C. Beaulieu C. Lafrenière J. J. Org. Chem. 2000, 65: 7091

Crossref Google Scholar
24 Kang S.-K. Cho D.-G. Park C.-H. Namkoong E.-Y. Shin J.-S. Synth. Commun. 1995, 25: 1659

Crossref Google Scholar
25 Smitrovich JH. Woerpel KA. J. Am. Chem. Soc. 1998, 120: 12998

Crossref Google Scholar
26 Smitrovich JH. Woerpel KA. J. Org. Chem. 2000, 65: 1601

Crossref Google Scholar
27 Didiuk MT. Morken JP. Hoveyda AH. J. Am. Chem. Soc. 1995, 117: 7273

Google Scholar
28 Visser MS. Hoveyda AH. Tetrahedron 1995, 51: 4383

Crossref Google Scholar
29 Visser MS. Heron NM. Didiuk MT. Sagal JF. Hoveyda AH. J. Am. Chem. Soc. 1996, 118: 4291

Crossref Google Scholar
30 Heron NM. Adams JA. Hoveyda AH. J. Am. Chem. Soc. 1997, 119: 6205

Crossref Google Scholar
31 Tominaga S. Oi Y. Kato T. An DK. Okamoto S. Tetrahedron Lett. 2004, 45: 5585

Google Scholar
32 Marino JP. Viso A. Lee J.-D. J. Org. Chem. 1997, 62: 645

Crossref Google Scholar
33 Oishi S. Kamano T. Niida A. Odagaki Y. Tamamura H. Otaka A. Hamanaka N. Fujii N. Org. Lett. 2002, 4: 1051

Crossref Google Scholar
34 Marino JP. Anna LJ. de la Pradilla RF. Martinez MV. Montero C. Viso A. J. Org. Chem. 2000, 65: 6462

Crossref Google Scholar
35 Murakami T. Shimizu T. Taguchi K. Tetrahedron 2000, 56: 533

Crossref Google Scholar
36 Taber DF. Mitten JV. J. Org. Chem. 2002, 67: 3847

Crossref Google Scholar
37 Moro FD. Crotti P. Bussolo VD. Macchia F. Pineschi M. Org. Lett. 2003, 5: 1971

Crossref Google Scholar
38 Betrozzi F. Crotti P. Moro FD. Bussolo VD. Macchia F. Pineschi M. Eur. J. Org. Chem. 2003, 1264

Crossref Google Scholar
39 Cantrill AA. Jarvis AN. Osborn HMI. Ouadi A. Sweeney JB. Synlett 1996, 847

Article in Thieme Connect Google Scholar
40 Aoyama H. Mimura N. Ohno H. Ishii K. Toda A. Tamamura H. Otaka A. Fujii N. Ibuka T. Tetrahedron Lett. 1997, 38: 7383

Crossref Google Scholar
41 Toda A. Aoyama H. Mimura N. Ohno H. Fujii N. Ibuka T. J. Org. Chem. 1998, 63: 7053

Crossref Google Scholar
42 Fujii N. Nakai K. Tamamura H. Otaka A. Mimura N. Miwa Y. Taga T. Yamamoto Y. Ibuka T. J. Chem. Soc., Perkin Trans. 1 1995, 1359

Crossref Google Scholar
43 Ibuka T. Mimura N. Ohno H. Nakai K. Akaji M. Habashita H. Tamamura H. Miwa Y. Taga T. Fujii N. Yamamoto Y. J. Org. Chem. 1997, 62: 2982

Crossref Google Scholar
44 Tammura H. Yamashita M. Nakajima Y. Sakano K. Otaka A. Ohno H. Ibuka T. Fujii N. J. Chem. Soc., Perkin Trans. 1 1999, 2983

Crossref Google Scholar
45 Oishi S. Niida A. Kamano T. Odagaki Y. Tamamura H. Otaka A. Hamanaka N. Fujii N. Org. Lett. 2002, 4: 1055

Crossref Google Scholar
46 Otaka A. Katagiri F. Kinoshita T. Odagaki Y. Oishi S. Tamamura H. Hamanaka N. Fujii N. J. Org. Chem. 2002, 67: 6152

Crossref PubMed Google Scholar
47 Caló V. Nacci A. Fiandanese V. Tetrahedron 1996, 52: 10799

Crossref Google Scholar
48 Katritzky AR. Zhang G. Jiang J. J. Org. Chem. 1995, 60: 7605

Crossref Google Scholar
49 Lautens M. Ma S. J. Org. Chem. 1996, 61: 7246

Crossref Google Scholar
50 Nakamura M. Hirai A. Nakamura E. J. Am. Chem. Soc. 2000, 122: 978

Crossref Google Scholar
51 Nakamura M. Matsuo K. Inoue T. Nakamura E. Org. Lett. 2003, 5: 1373

Crossref PubMed Google Scholar
52 Arrayas RG. Cabrera S. Carretero JC. Org. Lett. 2003, 5: 1333

Crossref Google Scholar
53 Arrayas RG. Cabrera S. Carretero JC. Org. Lett. 2005, 7: 219

Crossref PubMed Google Scholar
54 Surman MD. Mulvihill MJ. Miller MJ. Tetrahedron Lett. 2002, 43: 1131

Crossref Google Scholar
55 Spino C. Thibault C. Gingras S. J. Org. Chem. 1998, 63: 5283

Crossref Google Scholar
56 Gurjar MK. Nayak S. Ramana CV. Tetrahedron Lett. 2005, 46: 1881

Crossref Google Scholar
57 Gorins G. Kuhnert L. Johnson CR. Marnett LJ. J. Med. Chem. 1996, 39: 4871

Crossref Google Scholar
58 Petit M. Aubert C. Malacria M. Org. Lett. 2004, 6: 3937

Crossref Google Scholar
59 Spino C. Fréchette S. Tetrahedron Lett. 2000, 41: 8033

Crossref Google Scholar
60 Fürstner A. Méndez M. Angew. Chem. Int. Ed. 2003, 42: 5355

Crossref PubMed Google Scholar
61 Krause N. Morita N. Org. Lett. 2004, 6: 4121

Google Scholar
62 Ohno H. Toda A. Fujii N. Takemoto Y. Tanaka T. Ibuka T. Tetrahedron 2000, 56: 2811

Crossref Google Scholar
63 Tseng H.-R. Luh T.-Y. J. Org. Chem. 1996, 61: 8685

Crossref Google Scholar
64 Tseng H.-R. Lee C.-F. Yang L.-M. Luh T.-Y. J. Org. Chem. 1999, 64: 8582

Google Scholar
65 Bernard N. Chemla F. Normant JF. Tetrahedron Lett. 1999, 40: 1649

Crossref Google Scholar
66 Caporusso AM. Aronica LA. Geri R. Gori M. J. Organomet. Chem. 2002, 648: 109

Crossref Google Scholar
67a Naruse N. Tenmyo O. Kawano K. Tomita K. Ohgusa N. Miyaki T. Konishi M. Oki T. J. Antibiot. 1991, 44: 733

Crossref Google Scholar
67b Naruse N. Tsuno T. Sawada Y. Konishi M. Oki T. J. Antibiot. 1991, 44: 741

Crossref Google Scholar
67c Naruse N. Konishi M. Oki T. J. Antibiot. 1991, 44: 756

Crossref Google Scholar
67d Komita K. Oda N. Hoshino Y. Ohkusa N. Chikazawa H. J. Antibiot. 1991, 44: 940

Crossref Google Scholar
68 Houri AF. Xu Z. Cogan DA. Hoveyda AH. J. Am. Chem. Soc. 1995, 117: 2943

Crossref Google Scholar
69 Manker DC. Faulkner DJ. Tetrahedron 1987, 43: 3677

Crossref Google Scholar
70 Gao W.-G. Sakaguchi K. Isoe S. Ohfune Y. Tetrahedron Lett. 1996, 37: 7071

Crossref Google Scholar
71 Grove MD. Spencer GF. Rohwedder WK. Mandava N. Worley JF. Warthen JD. Steffens GL. Flippen-Anderson JL. Cook JC. Nature (London) 1979, 281: 216

Crossref Google Scholar
72 Marino JP. de Dios A. Anna LJ. Fernandez de la Pradilla R. J. Org. Chem. 1996, 61: 109

Crossref Google Scholar
73a Norman AW. Vitamin D, The Calcium Homeostatic Steroid Hormone Academic Press; New York: 1979.

Google Scholar
73b Norman AW. Koeffler HP. Bishop JE. Collins ED. Sergeev I. Zhou LX. Nemer I. Zhou J. Henry HL. Okamura WH. Vitamin D: Gene Regulation, Structurefunction Analysis and Clinical Application Norman AW. Bouillon R. Thomasset M. Walter de Gruyter; Berlin: 1991. p.146

Google Scholar
74 Terneiro M. Fall Y. Castedo L. Mouriño A. J. Org. Chem. 1997, 62: 6344

Crossref Google Scholar
75 Yang H. Sheng XC. Harrington EM. Ackermann K. Garcia AM. Lewis MD. J. Org. Chem. 1999, 64: 242

Crossref Google Scholar
76 Moncada S. Gryglewski R. Bunting S. Vane JR. Nature (London) 1976, 263: 663

Crossref Google Scholar
77 Wakita H. Matsumoto K. Yoshiwara H. Hosono Y. Hayashi R. Nishiyama H. Nagase H. Tetrahedron 1999, 55: 2449

Crossref Google Scholar
78 Wan Z. Nelson SG. J. Am. Chem. Soc. 2000, 122: 10470

Crossref Google Scholar
79 Cardllina JH. Moore RE. Arnold EV. Clardy J. J. Org. Chem. 1979, 44: 4039

Crossref Google Scholar
80 Chen K. Yang R. Wang C. Zhongcaoyao 1986, 17: 242 ; Chem. Abstr. 1986, 105, 130686a

Google Scholar
81 Yang D. Xu M. Org. Lett. 2001, 3: 1785

Crossref Google Scholar
82a Frank B. Gehrken H.-P. Angew. Chem. Int. Ed. 1980, 92: 484

Crossref Google Scholar
82b Ganguli M. Burka LT. Harris TM. J. Org. Chem. 1984, 49: 3762

Crossref Google Scholar
82c Mitchell P. FEBS Lett. 1977, 78: 1

Crossref Google Scholar
83 Krause N. Hoffmann-Röder A. Canisius J. Synthesis 2002, 1759

Article in Thieme Connect Google Scholar
84 Wirth D. Fischer-Lui I. Boland W. Icheln D. Runge T. König WA. Philips J. Clayton M. Helv. Chim. Acta 1992, 75: 734

Crossref Google Scholar
85 Singh SB. Zink DL. Liesch JM. Goetz MA. Jenkins RG. Nalin-Omstead M. Silverman KC. Bills GF. Mosley RT. Gibbs JB. Albers-Schonberg G. Lingham RB. Tetrahedron 1993, 49: 5917

Crossref Google Scholar
86 Enoki M. Watanabe T. Honda Y. Kawahara M. Chem. Lett. 2000, 54

Crossref Google Scholar
87a Kar A. Argade NP. J. Org. Chem. 2002, 67: 7131

Crossref Google Scholar
87b Baag MM. Kar A. Argade NP. Tetrahedron 2003, 59: 6489

Crossref Google Scholar
88 Weidenmuller H.-L. Cavagna F. Fehlhaber H.-W. Prave P. Tetrahedron Lett. 1972, 13: 3519

Crossref Google Scholar
89a Itoh S. Esaki N. Masaki K. Blank W. Soda K. J. Ferment. Bioeng. 1994, 77: 513

Google Scholar
89b Gama Y. Yasumoto M. Suzuki H. Ishigami Y. Yukagaku 1989, 38: 292 ; Chem. Abstr. 1990, 113, 99860s

Google Scholar
90a Kar A. Argade NP. Tetrahedron Lett. 2002, 43: 6563

Crossref Google Scholar
90b Kar A. Argade NP. Tetrahedron 2003, 59: 2991

Crossref Google Scholar
91 Rieu J.-P. Boucherle A. Cousse H. Mouzin G. Tetrahedron 1986, 15: 4095 ; and references cited therein

Google Scholar
92 Trissot-Croset K. Alexakis A. Tetrahedron Lett. 2004, 45: 7375

Crossref Google Scholar
93 Tsuda M. Izui N. Shimbo K. Sato M. Fukushi E. Kawabata J. Katsumata K. Horiguchi T. Kobayashi J. J. Org. Chem. 2003, 68: 5339

Crossref Google Scholar
94 Lepage O. Kattnig E. Fürstner A. J. Am. Chem. Soc. 2004, 126: 15970

Crossref Google Scholar

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