南极假丝酵母脂肪酶 B 催化的 1,3-二烷基-3-羟甲基氧化吲哚的动力学拆分。

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles.

机构信息

Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry-II, Guru Nanak Dev University, Amritsar, India.

Department of Chemistry, DAV University, Jalandhar, Punjab, India.

出版信息

Chirality. 2020 Dec;32(12):1377-1394. doi: 10.1002/chir.23284. Epub 2020 Nov 3.

DOI:10.1002/chir.23284

PMID:33141985

Abstract

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1'-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3'-indolin]-2'-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

摘要

南极假丝酵母（CAL-B）脂肪酶催化 1,3-二烷基-3-羟甲基氧化吲哚的对映选择性拆分，使用醋酸乙烯酯作为酰化剂和乙腈作为溶剂，可获得高达 99%ee 的（R）-1,3-二烷基-3-乙酰氧甲基氧化吲哚和高达 78%ee 的（S）-1,3-二烷基-3-羟甲基氧化吲哚，将（S）-3-烯丙基-3-羟甲基氧化吲哚转化为（3S）-1'-苄基-5-（碘甲基）-4,5-二氢-2H-螺[呋喃-3,3'-吲哚啉]-2'-酮。光学活性的 3-取代-3-羟甲基氧化吲哚和螺-氧化吲哚是合成潜在生物活性分子的关键合成子之一。