RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(4): 666-674
DOI: 10.1055/s-2006-926299
DOI: 10.1055/s-2006-926299
PAPER
© Georg Thieme Verlag Stuttgart · New YorkAn Efficient CuI-Promoted Synthesis of Tri- and Tetrasubstituted Alkenes Using Organozinc Species
Weitere Informationen
Received
27 July 2005
Publikationsdatum:
11. Januar 2006 (online)
Publikationsverlauf
Publikationsdatum:
11. Januar 2006 (online)

Abstract
An efficient method for the synthesis of multifunctionalized alkenes has been developed. In the presence of 5 mol% CuI as catalyst, organozinc species CF3COOZnEt, CF3COOZnMe and CF3COOZnPh reacted with α,β-acetylenic ketones and aldehydes in one pot providing trisubstituted alkenes in high yields with stereoselectivity. The reaction with β-substituted-α,β-acetylenic ketones gave tetrasubstituted alkenes in good yields with Z-isomers as the major products.
Key words
organozinc species - α,β-acetylenic ketones - aldehydes - multifunctionalized alkenes - CuI
- 1
Lee VJ. In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.139-168MissingFormLabel - 2
Wori M.Kuroda S.Dekura F. J. Am. Chem. Soc. 1999, 121: 5591 - 3a
Denmark SE.Choi JY. J. Am. Chem. Soc. 1999, 121: 5821 - 3b
Maezaki N.Sawamoto H.Yoshigami R.Suzuki T.Tanaka T. Org. Lett. 2003, 5: 1345 - 4a
Trost BM.Pinkerton AB. J. Am. Chem. Soc. 1999, 121: 1988MissingFormLabel - 4b
Trost BM.Pinkerton AB. Angew. Chem. Int. Ed. 2000, 39: 360MissingFormLabel - Reviews for the Morita-Baylis-Hillman reaction:
- 5a
Drewes SE.Roos GHP. Tetrahedron 1988, 44: 4653 - 5b
Basavaiah D.Darma RP.Hyma RS. Tetrahedron 1996, 52: 8001 - 5c
Langer P. Angew. Chem. Int. Ed. 2000, 39: 3049 - 5d
Basavaiah D.Rao AJ.Satyanarayana T. Chem. Rev. 2003, 103: 811 - 5e
Kataoka T.Kinoshita H. Eur. J. Org. Chem. 2005, 45 - 6a
Ciganek E. Org. React. (N.Y.) 1997, 51: 201 - 6b
Roth F.Gygax P.Frater G. Tetrahedron Lett. 1992, 48: 6371 - 6c
Drewes SE.Njamela OL.Emslie ND.Ramesar N.Field JS. Synth. Commun. 1993, 23: 2807 - 7
Marino JP.Linderman RJ. J. Org. Chem. 1983, 48: 4621 - 8a
Wei HX.Willis S.Li G. Tetrahedron Lett. 1998, 39: 8203 - 8b
Wei HX.Willis S.Li G. Synth. Commun. 1999, 29: 2959 - 9a
Wei HX.Hook JD.Fitzgerald KA.Li G. Tetrahedron: Asymmetry 1999, 10: 661 - 9b
Li G.Wei HX.Whittlesey BR.Bartrice NN. J. Org. Chem. 1999, 64: 1061 - 9c
Li G.Wei HX.Hook JD. Tetrahedron Lett. 1999, 40: 4611 - 9d
Li G.Kim SH.Wei HX. Tetrahedron 2000, 56: 719 - 10a
Ramachandran PV.Reddy MVR.Rudd MT.Alaniz JR. Tetrahedron Lett. 1998, 39: 8791 - 10b
Ramachandran PV.Ram Reddy MV.Rudd MT. Tetrahedron Lett. 1999, 40: 627 - 10c
Ramachandran PV.Ram Reddy MV.Rudd MT. Chem. Commun. 1999, 1979 - 10d
Li G.Wei HX.Willis S. Tetrahedron Lett. 1998, 39: 4607 - 10e
Chen D.Timmons C.Liu JY.Hendley A.Li G. Eur. J. Org. Chem. 2004, 3330 - 11
Yu S.Li NS.Kabalka GW. J. Org. Chem. 1999, 64: 5822 - For conjugate addition of zinc-copper reagents to acetylenic esters, see:
- 12a
Knochel P.Singer RD. Chem. Rev. 1993, 93: 2177 - 12b
Knoess HP.Furlong MT.Rozema MJ.Knochel P. J. Org. Chem. 1991, 56: 5974 - 12c
Jubert C.Knochel P. J. Org. Chem. 1992, 57: 5425 - For copper-catalyzed conjugate addition of zinc reagents to acetylenic esters, see:
- 13a
Crimmins MT.Nantermet P. J. Org. Chem. 1990, 55: 4235 - 13b
Crimmins MT.Nantermet P.Trotter BW.Vallin IM.Watson PS. J. Org. Chem. 1993, 58: 1038 - For conjugate addition of organozinc reagents to acetylenic ketones, see:
- 14a
Brunner M.Maas G. Synthesis 1995, 957 - 14b
Nakamura E.Kuwajima I. J. Am. Chem. Soc. 1984, 106: 3368 - 15a
Xue S.Li YL.Han KZ.Yin W.Wang M.Guo QX. Org. Lett. 2002, 4: 905 - 15b
Xue S.Han KZ.He L.Guo QX. Synlett 2003, 870 - 15c
Xue S.He L.Han KZ.Zheng XQ.Guo QX. Carbohydr. Res. 2005, 340: 303 - 16
Xue S.He L.Han KZ.Liu YK.Guo QX. Synlett 2005, 1247 - 17
Kitamura M.Miki T.Noyori R. Bull. Chem. Soc. Jpn. 2000, 73: 999 - 18a
Taniguchi M.Hino T.Kishi Y. Tetrahedron Lett. 1986, 27: 4767 - 18b
Taniguchi M.Kobayashi S.Nakagawa M.Hino T.Kishi Y. Tetrahedron Lett. 1986, 27: 4763 - 18c
Kinoshita S.Kinoshita H.Iwamura T.Watanabe S.Kataoka T. Chem. Eur. J. 2003, 9: 1496