Highly Diastereoselective Sequential Michael-Aldol Reactions of Methyl 2-Chloro-2-cyclopropylideneacetate with Grignard Reagents and Aldehydes

Suryakanta Dalai; Michael Limbach; Ligang Zhao; Markus Tamm; Madhumati Sevvana; Viktor V. Sokolov; Armin de Meijere

doi:10.1055/s-2006-926276

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Synthesis 2006(3): 471-479
DOI: 10.1055/s-2006-926276

PAPER

Highly Diastereoselective Sequential Michael-Aldol Reactions of Methyl 2-Chloro-2-cyclopropylideneacetate with Grignard Reagents and Aldehydes [1]

Suryakanta Dalai^a, Michael Limbach^a, Ligang Zhao^a, Markus Tamm^a, Madhumati Sevvana^b, Viktor V. Sokolov^a, Armin de Meijere*^a
^a Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany
Fax: +49(551)394795; e-Mail: ameijer1@gwdg.de;
^b Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany

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Publication History

Received 18 May 2005
Publication Date:
11 January 2006 (online)

Abstract
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Abstract

Grignard reagents, especially isopropylmagnesium chloride, smoothly undergo Michael addition onto methyl 2-bromo- and 2-chloro-2-cyclopropylideneacetate (1-Cl), and the thus formed magnesium enolates are particularly efficiently trapped with aromatic aldehydes. This one-pot reaction provides highly substituted chlorohydrines, mostly in high yields (10 out of 18 examples with 72-92%) and as pure (2S*,3R*)-diastereomers (anti-aldols). These chlorohydrines can be transformed to Darzens-type α,β-epoxyesters in good yields, as demonstrated for one example.

Key words

small ring systems - Michael additions - aldol reactions - domino reactions - diastereoselectivity - synthetic methods

References

1a
Part 119 in the series ‘Cyclopropyl Building Blocks for Organic Synthesis’.
1b
For part 118 see: Yucel, B.; Arve, L.; de Meijere, A. Tetrahedron 2005, 61, 11355.
1c
Part 117: Bräse, A.; Nüske, H.; Frank, D.; de Meijere, A. Eur. J. Org. Chem. 2005, 4167.
2a Liese T. Splettstösser G. de Meijere A. Angew. Chem., Int. Ed. Engl. 1982, 21: 790 ; Angew. Chem. 1982, 94, 799

Crossref Google Scholar
2b Liese T. Seyed-Mahdavi F. de Meijere A. Org. Synth. 1990, 69: 148

Crossref Google Scholar
2c For an advanced synthesis of 1-Br and 1-Cl see: Limbach M. Dalai S. de Meijere A. Adv. Synth. Catal. 2004, 346: 760

Crossref Google Scholar
For reviews see:
3a de Meijere A. Bull. Soc. Chim. Belg. 1984, 93: 241

Google Scholar
3b de Meijere A. Wessjohann L. Synlett 1990, 20

Google Scholar
3c de Meijere A. In New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC 5, Kyoto, Nov. 11-15, 1991) Oshiro Y. Kodansha; Tokyo: 1992. p.181

Google Scholar
3d de Meijere A. Kozhushkov SI. Hadjiarapoglou L. Top. Curr. Chem. 1999, 207: 149

Google Scholar
4a Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev. 2003, 103: 1213

Crossref Google Scholar
4b Nakamura I. Yamamoto Y. Adv. Synth. Catal. 2002, 344: 111

Crossref Google Scholar
5a Liese T. Teichmann S. de Meijere A. Synthesis 1988, 25

Crossref Google Scholar
5b Seyed-Mahdavi F. Teichmann S. de Meijere A. Tetrahedron Lett. 1986, 27: 6185

Crossref Google Scholar
6a Spitzner D. Engler A. Liese T. Splettstößer G. de Meijere A. Angew. Chem., Int. Ed. Engl. 1982, 21: 791 ; Angew. Chem. 1982, 94, 799

Crossref Google Scholar
6b Spitzner D. Engler A. Wagner P. de Meijere A. Bengtson G. Simon A. Peters K. Peters E.-M. Tetrahedron 1987, 43: 3213

Crossref Google Scholar
6c Hadjiarapoglou L. Klein I. Spitzner D. de Meijere A. Synthesis 1996, 525

Crossref Google Scholar
6d de Meijere A. Teichmann S. Seyed-Mahdavi F. Kohlstruk S. Liebigs Ann. 1996, 1989

Crossref Google Scholar
6e Wessjohann L. Giller K. Zuck B. Skattebøl L. de Meijere A. J. Org. Chem. 1993, 58: 6442

Crossref Google Scholar
6f Hadjiarapoglou L. de Meijere A. Seitz H.-J. Klein I. Spitzner D. Tetrahedron Lett. 1994, 35: 3269

Crossref Google Scholar
6g de Meijere A. Hadjiarapoglou LP. Noltemeyer M. Gutke H.-J. Klein I. Spitzner D. Eur. J. Org. Chem. 1998, 441

Crossref Google Scholar
7a de Meijere A. Teichmann S. Yu D. Kopf J. Oly M. von Thienen N. Tetrahedron 1989, 45: 2957

Crossref Google Scholar
7b Wessjohann L. Skattebøl L. de Meijere A. J. Chem. Soc., Chem. Commun. 1990, 574

Crossref Google Scholar
7c Giller K. Baird MS. de Meijere A. Synlett 1992, 524

Crossref Google Scholar
7d Es-Sayed M. Heiner T. de Meijere A. Synlett 1993, 57

Crossref Google Scholar
7e Zorn C. Goti A. Brandi A. Johnsen K. Kozhushkov SI. de Meijere A. Chem. Commun. 1998, 903

Crossref Google Scholar
7f Nötzel MW. Tamm M. Labahn T. Noltemeyer M. Es-Sayed M. de Meijere A. J. Org. Chem. 2000, 65: 3850

Crossref Google Scholar
7g Nötzel MW. Labahn T. Es-Sayed M. de Meijere A. Eur. J. Org. Chem. 2001, 3025

Crossref Google Scholar
7h Nötzel MW. Rauch K. Labahn T. de Meijere A. Org. Lett. 2002, 4: 839

Crossref Google Scholar
7i Zorn C. Goti A. Brandi A. Johnsen K. Noltemeyer M. Kozhushkov SI. de Meijere A. J. Org. Chem. 1999, 64: 755

Crossref Google Scholar
8a Wessjohann L. McGaffin G. de Meijere A. Synthesis 1989, 359

Crossref Google Scholar
8b Wessjohann L. Krass N. Yu D. de Meijere A. Chem. Ber. 1992, 125: 867

Crossref Google Scholar
8c Es-Sayed M. Gratkowski C. Krass N. Meyers AI. de Meijere A. Synlett 1992, 962

Crossref Google Scholar
8d Es-Sayed M. G ratkowski C. Krass N. Meyers AI. de Meijere A. Tetrahedron Lett. 1993, 34: 289

Crossref Google Scholar
8e Tamm M. Thutewohl M. Ricker CB. Bes MT. de Meijere A. Eur. J. Org. Chem. 1999, 2017

Crossref Google Scholar
9a Belov VN. Funke C. Labahn T. Es-Sayed M. de Meijere A. Eur. J. Org. Chem. 1999, 1345

Crossref Google Scholar
9b Funke C. Es-Sayed M. de Meijere A. Org. Lett. 2000, 2: 4249

Crossref Google Scholar
9c Limbach M. Dalai S. Janssen A. Es-Sayed M. Magull J. de Meijere A. Eur. J. Org. Chem. 2005, 610

Crossref Google Scholar
Reviews see:
10a Gawley RE. Synthesis 1976, 777

Crossref PubMed Google Scholar
10b Notz W. Tanaka F. Barbas CF. Acc. Chem. Res. 2004, 37: 580

Crossref PubMed Google Scholar
11a Posner GH. Chem. Rev. 1986, 86: 831

Crossref PubMed Google Scholar
11b Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Engl. 1993, 32: 131 ; Angew. Chem. 1993, 105, 137

Crossref PubMed Google Scholar
11c Tietze LF. Chem. Rev. 1996, 96: 115

Crossref PubMed Google Scholar
Recent examples:
12a Barrett AGM. Kamimura A. J. Chem. Soc., Chem. Commun. 1995, 17: 1755

Google Scholar
12b Tsukada N. Nishimura TK. Tsubouchi H. Ono M. Hayama T. Nagaoka Y. Tomioka K. Tetrahedron Lett. 2003, 44: 2323

Google Scholar
12c Tsukada N. Shimida T. Gyoung YS. Asao N. Yamamoto Y. J. Org. Chem. 1995, 60: 143

Google Scholar
Recent examples:
13a Hara O. Sugimoto K. Makino K. Hamada Y. Synlett 2004, 1625

Crossref Google Scholar
13b Rao HSP. Senthilkumar SP. J. Org. Chem. 2004, 69: 2591

Crossref Google Scholar
13c Makino K. Hara O. Takiguchi Y. Katano T. Asakawa Y. Hatano K. Hamada Y. Tetrahedron Lett. 2003, 44: 8925

Crossref Google Scholar
13d Huang X. Xiong Z.-C. Chem. Commun. 2003, 14: 1714

Crossref Google Scholar
13e Yamamoto Y. Momiyama N. Yamamoto H. J. Am. Chem. Soc. 2004, 126: 5962

Crossref Google Scholar
Recent examples:
14a Paulsen H. Antons S. Brandes A. Lögers M. Müller SN. Naab P. Schmeck C. Schneider S. Stoltefuß J. Angew. Chem. Int. Ed. 1999, 38: 3373 ; Angew. Chem. 1999, 111, 3574

PubMed Google Scholar
14b Schneider C. Reese O. Angew. Chem. Int. Ed. 2000, 39: 2948 ; Angew. Chem. 2000, 112, 3074

PubMed Google Scholar
14c Kamimura A. Mitsudera H. Omata Y. Matsuura K. Shirai M. Kakehi A. Tetrahedron 2002, 58: 9817

PubMed Google Scholar
14d Huang X. Xie MH. Org. Lett. 2002, 4: 1331

PubMed Google Scholar
14e Huang X. Xie MH. J. Org. Chem. 2002, 67: 8895

PubMed Google Scholar
14f Arai T. Sasai H. Aoe K.-I. Okamura K. Date T. Shibasaki M. Angew. Chem., Int. Ed. Engl. 1996, 35: 104 ; Angew. Chem. 1996, 108, 103

PubMed Google Scholar
14g Halland N. Aburel PS. Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1272 ; Angew. Chem. 2004, 116, 1292

PubMed Google Scholar
15a Satoh T. Kitoh Y. Onda K.-I. Takana K. Yamakawa K. Tetrahedron 1994, 50: 4957

Crossref Google Scholar
15b Evans DA. Tedrow JS. Shaw JT. Downey CW. J. Am. Chem. Soc. 2002, 124: 392

Crossref Google Scholar
16a Thibonnet J. Knochel P. Tetrahedron Lett. 2000, 41: 3319

Crossref Google Scholar
16b Thibonnet J. Vu VA. Berillon L. Knochel P. Tetrahedron 2002, 58: 4787

Crossref Google Scholar
18 Chandrasekhar S. Narsihmulu C. Reddy MR. Reddy MS. Tetrahedron Lett. 2003, 44: 2583

Crossref Google Scholar
19 Sokolov V.V. Es-Sayed M. De Meijere A. unpublished results

17

Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited as supplementary publication no. CCDC-268832 with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk].