通过氮杂环丁烷鎓离子催化的 Diels-Alder/反-Diels-Alder 序列对烯丙醇进行对映选择性合成。
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed Diels-Alder/Retro-Diels-Alder sequence.
机构信息
Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield S3 7HF, UK.
出版信息
Org Lett. 2009 Nov 19;11(22):5358-61. doi: 10.1021/ol902280d.
PMID:19856904
Abstract
A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels-Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to access secondary and tertiary allylic alcohols in good to high enantiomeric excess via a cycloreversion by flash vacuum pyrolysis.
摘要
三氟甲脒激活的噁唑硼烷催化剂成功地促进了 9-甲基蒽与甲基丙烯醛的不对称 Diels-Alder 反应，具有高区域和对映选择性。所得环加成物随后被用作手性模板，通过快速真空热解进行环重排，以良好到高对映过量获得仲和叔烯丙醇。
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