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Synthesis 2008(1): 69-74
DOI: 10.1055/s-2007-990903
DOI: 10.1055/s-2007-990903
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Chiral Pyridyl Alcohols Using a Two-Step Catalytic Approach
Further Information
Received
14 September 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)
Abstract
Chiral pyridyl alcohols have been prepared by developing a two-step approach that uses the asymmetric cyanation of aldehydes to give cyanohydrins and subsequent [2+2+2]-cyclotrimerization reaction with acetylene.
Key words
asymmetric synthesis - cyclotrimerization - cyanohydrin - pyridine - aldehyde
- 1a
Heller B.Hapke M. Chem. Soc. Rev. 2007, 36: 1085 ; and references cited therein - 1b
Chopade PR.Louie J. Adv. Synth. Catal. 2006, 348: 2307 - 1c
Kotha S.Brahmachary E.Lahiri K. Eur. J. Org. Chem. 2005, 4741 - 1d
Varela JA.Saá C. Chem. Rev. 2003, 103: 3787 - 1e
Dzhemilev UM.Selimov FA.Tolstikov GA. ARKIVOC 2001, (ix): 85 ; http://www.arkat-usa.org/home - 2a
Chelucci G. Tetrahedron: Asymmetry 1995, 6: 811Reference Ris Wihthout Link - 2b
Falorni M.Chelucci G.Conti S.Giacomelli G. Synthesis 1992, 972Reference Ris Wihthout Link - 2c
Chelucci G.Falorni M.Giacomelli G. Synthesis 1990, 1121Reference Ris Wihthout Link - 2d
Botteghi C.Chelucci G. Gazz. Chim. Ital. 1989, 119: 71Reference Ris Wihthout Link - 2e
Azzena U.Chelucci G.Delogu G.Gladiali S.Marchetti M.Soccolini F.Botteghi C. Gazz. Chim. Ital. 1986, 116: 307Reference Ris Wihthout Link - 2f
Tatone D.Dich TC.Nacco R.Botteghi C. J. Org. Chem. 1975, 40: 2987Reference Ris Wihthout Link - 3a
Heller B.Gutnov A.Fischer C.Drexler H.-J.Spannenberg A.Redkin D.Sundermann C.Sundermann B. Chem. Eur. J. 2007, 13: 1117Reference Ris Wihthout Link - 3b
Gutnov A.Heller B.Fischer C.Drexler H.-J.Spannenberg A.Sundermann B.Sundermann C. Angew. Chem. Int. Ed. 2004, 43: 3795 ; Angew. Chem. 2004, 116, 3883Reference Ris Wihthout Link - 4a
Heller B.Sundermann B.Fischer C.You J.Chen W.Drexler H.-J.Knochel P.Bonrath W.Gutnov A. J. Org. Chem. 2003, 68: 9221 - 4b
Heller B.Sundermann B.Buschmann H.Drexler H.-J.You J.Holzgrabe U.Heller D.Oehme G. J. Org. Chem. 2002, 67: 4414 - 4c
Heller B.Heller D.Oehme G. J. Mol. Catal. A 1996, 110: 211 - 4d
Heller B.Oehme G. J. Chem. Soc., Chem. Commun. 1995, 179 - Overviews on the synthetic chemistry and preparation of cyanohydrins:
- 5a
Chen FX.Feng X. Curr. Org. Chem. 2006, 3: 77 - 5b
Brunel J.-M.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 ; Angew. Chem. 2004, 116, 2810 - 5c
North M. Tetrahedron: Asymmetry 2003, 14: 147 - 5d
Gregory RJH. Chem. Rev. 1999, 99: 3649 - 5e
Effenberger F. Angew. Chem. Int. Ed. 1994, 33: 1555 ; Angew. Chem. 1994, 106, 1609 - 5f
North M. Synlett 1993, 807 - Recent examples on the asymmetric synthesis of pyridyl alcohols using transition-metal complexes:
- 6a
Mazet C.Roseblade S.Koehler V.Pfaltz A. Org. Lett. 2006, 8: 1879 - Hydrogenation:
- 6b
Chen C.Reamer RA.Chilenski JR.McWilliams CJ. Org. Lett. 2003, 5: 5039 - 6c
Ohkuma T.Koizumi M.Yoshida M.Noyori R. Org. Lett. 2000, 2: 1749 - 6d
Okano K.Murata K.Ikariya T. Tetrahedron Lett. 2000, 41: 9277 - 6e
Burk MJ.Hems W.Herzberg D.Malan C.Zanotti-Gerosa A. Org. Lett. 2000, 2: 4173 - Use of pyridyl alcohols in synthesis and catalysis; epoxidation of allylic alcohols:
- 6f
Hawkins JM.Sharpless KB. Tetrahedron Lett. 1987, 28: 2825 - Conjugate addition of dialkylzinc reagents to α,β-unsaturated ketones:
- 6g
Bolm C.Ewald M. Tetrahedron Lett. 1990, 31: 5011 - 6h
Bolm C. Tetrahedron: Asymmetry 1991, 2: 701 - 6i
Bolm C.Ewald M.Felder M. Chem. Ber. 1992, 125: 1205 - Nucleophilic addition of dialkylzinc reagents to aldehydes:
- 6j
Ishizaki M.Fujita K.Shimamoto M.Hoshino O. Tetrahedron: Asymmetry 1994, 5: 411 - 6k
Ishizaki M.Hoshino O. Tetrahedron: Asymmetry 1994, 5: 1901 - 6l
Ishizaki M.Hoshino O. Chem. Lett. 1994, 1337 - 6m
Bolm C.Schlingo H.Harms K. Chem. Ber. 1992, 125: 1191 - 6n
Chelucci G.Soccolini F. Tetrahedron: Asymmetry 1992, 3: 1235 - Asymmetric hydrogenation:
- 6o
Drury WJ.Zimmermann N.Keenan M.Hayashi M.Kaiser S.Goddard R.Pfaltz A. Angew. Chem. Int. Ed. 2004, 43: 70 ; Angew. Chem. 2004, 116, 72 - 7 Recent review:
Achard TRJ.Clutterbuck LA.North M. Synlett 2005, 1828 - 8a
Belokon YN.Green B.Ikonnikov NS.North M.Parsons T.Tararov VI. Tetrahedron 2001, 57: 771 - 8b
Belokon YN.Green B.Ikonnikov NS.Larichev VS.Lokshin BV.Moscalenko MA.North M.Orizu C.Peregudov AS.Timofeeva GI. Eur. J. Org. Chem. 2000, 2655 - 8c
Belokon YN.North M.Parsons T. Org. Lett. 2000, 2: 1617 - 8d
Belokon YN.Caveda-Cepas S.Green B.Ikonnikov NS.Khrustalev VN.Larichev VS.Moscalenko MA.North M.Orizu C.Tararov VI.Tasinazzo M.Timofeeva GI.Yashkina LV. J. Am. Chem. Soc. 1999, 121: 3968 - 9a
Belokon YN.Gutnov AV.Moskalenko MA.Yashkina LV.Lesovoy DE.Ikonnikov NS.Larichev VS.North M. Chem. Commun. 2002, 244 - 9b
Belokon YN.Carta P.Gutnov AV.Maleev V.Moskalenko MA.Yashkina LV.Ikonnikov NS.Voskoboev NV.Khrustalev VN.North M. Helv. Chim. Acta 2002, 85: 3301 - 10
Belokon YN.Blacker AJ.Clutterbuck LA.North M. Org. Lett. 2003, 5: 4505 - 11
Lundgren S.Wingstrand E.Penhoat M.Moberg C. J. Am. Chem. Soc. 2005, 127: 11592 - 12
Veum L.Kuster M.Telalovic S.Hanefeld U.Maschmeyer T. Eur. J. Org. Chem. 2002, 1516 - 13
Schmidt M.Hervé S.Klempier N.Griengl H. Tetrahedron 1996, 52: 7833 - Reported data: Optical rotation:
- 14a
Abiko A.Wang G.-Q. Tetrahedron 1998, 54: 11405 - NMR:
- 14b
Harle H.Jochims JC. Chem. Ber. 1986, 119: 1400 - 14c
Rasmussen JK.Heilmann SM. Synthesis 1978, 219 - 14d
Hünig S.Wehner G. Chem. Ber. 1980, 113: 324 - 14e
Dünnwald T.Demir AS.Siegert P.Pohl M.Müller M. Eur. J. Org. Chem. 2000, 2161 - 15
Bojadziev SE.Tsankov DT.Ivanov PM.Berova ND. Bull. Chem. Soc. Jpn. 1987, 2651 - 16
Ágai B.Proszenyák Á.Tárkányi G.Vida L.Faigl F. Eur. J. Org. Chem. 2004, 3623 - 17
Ishizaki M.Fujita K.Shimamoto M.Hoshino O. Tetrahedron: Asymmetry 1994, 5: 411