Design of C3‐Alkenyl‐Substituted 2‐Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov‐Type Cyclization

The C3‐alkenyl‐substituted 2‐indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov‐type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Brønsted acid, the interrupted Nazarov‐type cyclization of C3‐alkenyl‐substituted 2...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-03, Vol.360 (5), p.846-851
Main Authors: Wang, Cong‐Shuai, Wu, Jia‐Le, Li, Can, Li, Lin‐Zhi, Mei, Guang‐Jian, Shi, Feng
Format: Article
Language:English
Subjects:
asymmetric organocatalysis
Catalysis
cyclization
enantioselectivity
indolylmethanol
Nucleophiles
Phosphoric acid
Substitutes
Substrates
tandem reaction
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Summary:The C3‐alkenyl‐substituted 2‐indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov‐type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Brønsted acid, the interrupted Nazarov‐type cyclization of C3‐alkenyl‐substituted 2‐indolylmethanols with nucleophiles occurred smoothly to construct cyclopenta[b]indole frameworks in generally excellent diastereo‐ and enantioselectivities (up to >95:5 dr, >99% ee).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701521