New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

被引：97

作者：

Sumida, S ^{[1
]}

Ohga, M ^{[1
]}

Mitani, J ^{[1
]}

Nokami, J ^{[1
]}

机构：

[1] Okayama Univ Sci, Dept Appl Chem, Okayama 7000005, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2000年 / 122卷 / 07期

关键词：

D O I：

10.1021/ja990057p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gamma-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals I. were convened to the corresponding alpha-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti- and syn-gamma-adducts 3 gave E- and Z-alpha-adducts 6, respectively, and the optical purity of the gamma-adducts 3 was transferred to the alpha-adducts 6 with >98%ee. This suggests that the allyl-transfer reaction proceeds stereoselectively via six-membered cyclic transition states [T]. The reaction was catalyzed by various metal triflates as well as Lewis acids and Bronsted acids.

引用

页码：1310 / 1313

页数：4

共 43 条

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