Cation-Directed Enantioselective N-Functionalization of Pyrroles

被引：24

作者：

Armstrong, Roly J. ^{[1
]}

D'Ascenzio, Melissa ^{[1
]}

Smith, Martin D. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

SYNLETT | 2016年 / 27卷 / 01期

基金：

欧洲研究理事会;

关键词：

pyrroles; phase-transfer catalysis; organocatalysis; asymmetric synthesis; chiral aminals; PHASE-TRANSFER CATALYSIS; FRIEDEL-CRAFTS ALKYLATION; BRONSTED-ACID CATALYSIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; RING-CLOSURE; NUCLEOPHILES; HYDROXIDE; ALDEHYDES; INDOLES;

D O I：

10.1055/s-0035-1560813

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective N-functionalization of pyrroles has been developed. Imines formed in situ via condensation underwent cation-directed cyclization with complete N-regioselectivity. The cyclized products were obtained with enantiomeric ratios up to 96:4 for aldimine substrates and up to 99:1 for trifluoromethyl ketimines. The reaction proceeds without an acidifying group on the pyrrole and offers a new approach to the generation of chiral nonracemic aminals.

引用

页码：6 / 10

页数：5

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