A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine

被引：0

作者：

Pareek, Archana ^{[1
]}

Khom, Sonam Tashi ^{[1
]}

Saikia, Pranjit ^{[1
]}

Yadav, Nagendra Nath ^{[1
]}

机构：

[1] North Eastern Reg Inst Sci & Technol NERIST, Dept Chem, Nirjuli 791109, Arunachal Prade, India

来源：

MONATSHEFTE FUR CHEMIE | 2024年 / 155卷 / 05期

关键词：

Chiral aziridines; Ring strain; Bicyclic aziridinium ion; Ring expansion; Pipecolic acid; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PIPERIDINE ALKALOIDS; CONCISE; NUCLEOPHILES; REACTIVITY; RESOLUTION; EPOXIDES;

D O I：

10.1007/s00706-024-03187-3

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring expansion of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butyl tosylate obtained from tosylation of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butan-1-ol via formation of 1-azabicyclo[4.1.0]heptane tosylate gives substituted piperidine. The ring openings of azabicycloheptane tosylate with acetate nucleophiles proceeded in highly regio- and stereoselective manner with release of the ring-strain of the three-membered aziridine ring through the breakage of either C-N bond. This ring expansion streategy of aziridine provides a short route for asymmetric synthesis of biologically active natural alkaloid such as (R)-pipecolic acid.

引用

页码：525 / 529

页数：5

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