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Enantioselective Synthesis of 4 H ‐Pyrans Through Organocatalytic Asymmetric Formal [3+3] Cycloadditions of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones with β‐Keto Esters
Author(s) -
Yue Zhenting,
Li Wenbo,
Liu Lu,
Wang Cuihong,
Zhang Junliang
Publication year - 2016
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.201600591
Subject(s) - chemistry , enantioselective synthesis , formal synthesis , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
4 H ‐Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2‐(1‐alkynyl)‐2‐alken‐1‐ones and β‐keto esters catalyzed by a cyclohexyldiamine‐based thiourea‐tertiary amine bifunctional catalyst. Under the mild and eco‐friendly conditions, a wide range of polysubstituted 4 H ‐pyrans were obtained in moderate yields with good enantioselectivities.