通过烷氧基硼酸酯的分子内氧杂 - 迈克尔反应实现1-和3-取代异苯并二氢吡喃的有机催化对映选择性合成：（+）-索奈哌唑的合成
Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole.
作者信息
Raveendra Barnala, Maity Sanjay, Das Braja Gopal, Ghorai Prasanta
机构信息
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal-462066, India.
出版信息
J Org Chem. 2015 Jul 17;80(14):7008-18. doi: 10.1021/acs.joc.5b00719. Epub 2015 Jul 7.
PMID:26102523
Abstract
The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.
摘要
结果表明，使用手性双功能有机催化剂，烷氧基硼酸酯策略的对映选择性氧杂-迈克尔反应为对映体富集的1-和3-取代异苯并二氢吡喃提供了一条新的实用路线。此外，该方法还扩展到多巴胺受体拮抗剂(+)-索奈哌唑的对映选择性合成。
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