Highly enantioselective intermolecular Cu (I)-catalyzed cyclopropanation of cyclic enol ethers. Asymmetric total synthesis of (+)-Quebrachamine

O Temme, SA Taj, PG Andersson

Index: Temme, Oliver; Taj, Shabbir-Ali; Andersson, Pher G. Journal of Organic Chemistry, 1998 , vol. 63, # 17 p. 6007 - 6015

Full Text: HTML

Citation Number: 61

Abstract

A set of cyclic enol ethers derived from 2, 3-dihydrofuran 35 and 3, 4-dihydropyran 8 with a varying substitution pattern at the olefinic system were synthesized. Evans's ligand 5 with Cu (I) OTf was found to be an effective catalyst in the cyclopropanation reaction between cyclic enol ethers 14, 19, 28-31, and 33 and ethyl diazoacetate 6 to give diastereoselectivities up to exo/endo= 95: 5 and enantioselectivities higher than 95% in nearly all cases. Because ...

Related Articles:

Wittig and horner-wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis

[Ley, Steven V.; Lygo, Barry; Organ, Helen M.; Wonnacott, Anne Tetrahedron, 1985 , vol. 41, # 18 p. 3825 - 3836]

Wittig and horner-wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis

[Ley, Steven V.; Lygo, Barry; Organ, Helen M.; Wonnacott, Anne Tetrahedron, 1985 , vol. 41, # 18 p. 3825 - 3836]

Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis

[Ley, Steven V.; Lygo, Barry; Sternfeld, Francine; Wonnacott, Anne Tetrahedron, 1986 , vol. 42, # 15 p. 4333 - 4342]

Wittig and horner-wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis

[Ley, Steven V.; Lygo, Barry; Organ, Helen M.; Wonnacott, Anne Tetrahedron, 1985 , vol. 41, # 18 p. 3825 - 3836]

Wittig and horner-wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis

[Ley, Steven V.; Lygo, Barry; Organ, Helen M.; Wonnacott, Anne Tetrahedron, 1985 , vol. 41, # 18 p. 3825 - 3836]

More Articles...