Concise synthesis of optically pure syn-1,3-diols by stereoselective desymmetrization of a divinylcarbinol

被引：7

作者：

Berkenbusch, T

Brückner, R

机构：

[1] Bayer AG, BCH, FCH, RD,LP2, D-51368 Leverkusen, Germany

[2] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

SYNLETT | 2003年 / 12期

关键词：

acetonides; desymmetrization; 1,3-diols; epoxyalcohols; Sharpless asymmetric epoxidation;

D O I：

10.1055/s-2003-41487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Divinylcarbinols 17 and 18, CS-symmetrical and cis-configured, were desymmetrized by Sharpless' asymmetric epoxidation. This furnished anti-configured monoepoxy alcohols 19 (85% ee) and 20 (94% ee), respectively, or their minor images (ent-19, 84% ee: ent-20, 95% ee). 20 (ent-20) was reduced by Red-Al(R) regio- and chemoselectively, providing syn-1,3-diols ent-21 (21) at low and ent-22 (22) at higher temperature (94-95% ee). They should allow the obtention of more elaborated syn-1,3-diols.

引用

页码：1813 / 1816

页数：4

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