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由(3S,5R,7aR)-5-(苯并三唑-1-基)-3-苯基[2,1-b]恶唑并吡咯烷不对称合成2-取代和2,5-二取代吡咯烷。

Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3S,5R,7aR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine.

作者信息

Katritzky Alan R., Cui Xi-Lin, Yang Baozhen, Steel Peter J.

机构信息

Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, and Department of Chemistry, University of Canterbury, Christchurch, New Zealand.

出版信息

J Org Chem. 1999 Mar 19;64(6):1979-1985. doi: 10.1021/jo9821426.

DOI:10.1021/jo9821426
PMID:11674292
Abstract

Benzotriazole, 2,5-dimethoxytetrahydrofuran, and (S)-phenylglycinol in one step gave 80% of (3S, 5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl-[2,1-b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5-disubstituted pyrrolidines.

摘要

苯并三唑、2,5 - 二甲氧基四氢呋喃和(S)-苯甘醇一步反应生成80%的(3S, 5R,7aR)-5-(苯并三唑 - 1 - 基)-3 - 苯基 - [2,1 - b]恶唑并吡咯烷(6),其晶体结构通过X射线晶体学得到证实。新型手性吡咯烷合成子6与有机硅(烯丙基三甲基硅烷和乙烯氧基三甲基硅烷)、有机磷、有机锌和格氏试剂反应,得到手性2 - 取代和2,5 - 二取代吡咯烷。

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