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A Highly Effective Bis(sulfonamide)–Diamine Ligand: A Unique Chiral Skeleton for the Enantioselective Cu‐Catalyzed Henry Reaction
Author(s) -
Jin Wei,
Li Xincheng,
Huang Yongbo,
Wu Fan,
Wan Boshun
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.201000964
Subject(s) - sulfonamide , nitromethane , enantioselective synthesis , nitroaldol reaction , diamine , ligand (biochemistry) , catalysis , chemistry , combinatorial chemistry , organic chemistry , biochemistry , receptor
A skeleton in the closet! As a unique chiral skeleton, the newly developed bis(sulfonamide)–diamine, which contains both diamine and bis(sulfonamide) moieties, was a highly effective ligand for the asymmetric Cu(OAc) 2 ‐catalyzed Henry reaction between nitromethane and aldehydes with a low catalyst loading at room temperature (see scheme). Both aliphatic and aromatic aldehydes gave excellent enantioselectivities of up to 99 % ee.