Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

被引：98

作者：

Gonzalez, A ^{[1
]}

Aiguade, J ^{[1
]}

Urpi, F ^{[1
]}

Vilarrasa, J ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC QUIM,DEPT QUIM ORGAN,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(96)02055-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：8949 / 8952

页数：4

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