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
收藏
页码：1813 / 1816
页数：4
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