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Catalytic Asymmetric [4+2] Cyclization of para ‐Quinone Methide Derivatives with 3‐Alkyl‐2‐vinylindoles
Author(s) -
Jiang XiaoLi,
Wu ShuFang,
Wang JinRong,
Mei GuangJian,
Shi Feng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800829
Subject(s) - chemistry , catalysis , alkyl , quinone methide , enantioselective synthesis , phosphoric acid , combinatorial chemistry , quinone , medicinal chemistry , organic chemistry
A catalytic asymmetric [4+2] cyclization of para ‐quinone methide (p‐QM) derivatives with 3‐alkyl‐2‐vinylindoles in the presence of a chiral phosphoric acid has been established, and this method provides chiral chroman frameworks in good yields (up to 98%) with high diastereoselectivities (up to >95:5 dr ) and excellent enantioselectivities (up to 96% ee ). This reaction represents the first catalytic asymmetric [4+2] cyclization of p‐QM derivatives with electron‐rich alkenes, which will enrich the field of catalytic asymmetric reactions of p‐QM derivatives. In addition, this catalytic asymmetric cyclization was successfully applied to 3‐alkyl‐2‐vinylindoles. More importantly, this reaction will offer a useful method for the construction of enantioenriched chroman frameworks.