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An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons
Author(s) -
Cao ChunLi,
Zhou YouYun,
Zhou Jian,
Sun XiuLi,
Tang Yong,
Li YuXue,
Li GuangYu,
Sun Jie
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900696
Subject(s) - bicyclic molecule , tandem , organocatalysis , chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , organic chemistry , materials science , composite material
Cyclic ketones react with ( E )‐2‐nitroallylic acetates in the presence of catalytic pyrrolidine‐thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98 % ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.