D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions

被引：30

作者：

Lutzen, A ^{[1
]}

Koll, P ^{[1
]}

机构：

[1] UNIV OLDENBURG,DEPT CHEM,ORGAN CHEM LAB,D-26111 OLDENBURG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(97)00096-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral N-acylated oxazolidin-2-one derivatives from D-xylose have been shown to undergo diastereoselective aldol reactions via their lithium imide enolates to afford beta-hydroxylated products. Aliphatic substrates and aldehydes were shown to yield 'non-Evans' syn-aldols readily interpreted by assuming chelated chair-like transition states. When substrates and aldehydes bearing aromatic groups are used chelated boat- or twist-boat-like transition states seem to become similarly or even more probable so that anti- or syn-aldols are also formed from cis- or trans-enolates, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：1193 / 1206

页数：14

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