Diastereoselective Michael addition of (S)-mandelic acid enolate to nitroalkenes.: Enantioselective synthesis of α-hydroxy-α,β-diaryl-γ-lactams

被引：19

作者：

Blay, G ^{[1
]}

Fernández, I ^{[1
]}

Monje, B ^{[1
]}

Pedro, JR ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 01期

关键词：

nitrostyrenes; 1,4-addition; dioxolanone; GABA; self-regeneration of stereocenters;

D O I：

10.1016/j.tet.2003.10.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the lithium enolate of the (S,S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several aromatic nitroalkenes in the presence of HMPA proceeds readily to give the corresponding Michael adducts in good yields and diastereoselectivities. Reduction of the nitro group with Zn/HCl/EtOH/H2O with concomitant intramolecular aminolysis of the acetal moiety leads directly to enantiomerically pure alpha-hydroxy-alpha,beta-diaryl-gamma-lactams. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：165 / 170

页数：6

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