Diastereoselective additions of chiral vinylzinc reagents to α-chiral aldehydes

被引：40

作者：

Marshall, JA ^{[1
]}

Eidam, P ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 03期

关键词：

D O I：

10.1021/ol0363568

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Additions of vinylic zinc bromide reagents to alpha-chiral aldehydes (R-1 = CH2OTBS, R-2 = Me; R-1 = Me, R-2 = OTBS) in the presence of lithiated (+) or (-) N-methylephedrine proceed with predominant reagent control to afford anti or syn adducts stereoselectively, except when the aldehydes possess an alkoxy substituent at the alpha or beta-positions (R-1 = Me, R-1 = OBn; R-1 = CH2OBn, R-2 = Me), in which case chelation-controlled adducts predominate.

引用

页码：445 / 448

页数：4

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