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Physical Organic Study of Structure–Activity–Enantioselectivity Relationships in Asymmetric Bifunctional Thiourea Catalysis: Hints for the Design of New Organocatalysts
Author(s) -
Li Xin,
Deng Hui,
Zhang Bo,
Li Jiuyuan,
Zhang Long,
Luo Sanzhong,
Cheng JinPei
Publication year - 2010
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.200902430
Subject(s) - bifunctional , thiourea , catalysis , enantioselective synthesis , stereoselectivity , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , computer science
Acidity effect : Correlations of p K a with catalytic activity and stereoselectivity were determined and linear free energy relationships (LFERs) were observed for both p K a −log ( k ) and p K a −log ( R / S ) correlations in meta ‐ and/or para ‐substituted aromatic thioureas (see figure). These results provided a basis for new catalyst development and several improved catalysts were identified in our initial attempts.