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Chiral Metal–Organic Frameworks Bearing Free Carboxylic Acids for Organocatalyst Encapsulation
Author(s) -
Liu Yan,
Xi Xiaobing,
Ye Chengcheng,
Gong Tengfei,
Yang Zhiwei,
Cui Yong
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408896
Subject(s) - chemistry , enantiopure drug , aldol reaction , mesoporous material , stereoselectivity , organocatalysis , carboxylic acid , catalysis , metal organic framework , organic chemistry , combinatorial chemistry , enantioselective synthesis , adsorption
Two chiral carboxylic acid functionalized micro‐ and mesoporous metal–organic frameworks (MOFs) are constructed by the stepwise assembly of triple‐stranded heptametallic helicates with six carboxylic acid groups. The mesoporous MOF with permanent porosity functions as a host for encapsulation of an enantiopure organic amine catalyst by combining carboxylic acids and chiral amines in situ through acid–base interactions. The organocatalyst‐loaded framework is shown to be an efficient and recyclable heterogeneous catalyst for the asymmetric direct aldol reactions with significantly enhanced stereoselectivity in relative to the homogeneous organocatalyst.