Premium
New adaptive chiral thiophene ligands for copper‐catalyzed asymmetric Henry reaction
Author(s) -
Bandini Marco,
Cabiddu Salvatore,
Cadoni Enzo,
Olivelli Pasquale,
Sinisi Riccardo,
UmaniRonchi Achille,
Usai Michele
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20613
Subject(s) - chemistry , nitromethane , thiophene , enantioselective synthesis , catalysis , chirality (physics) , nitroaldol reaction , enantiomer , enantiomeric excess , combinatorial chemistry , copper , stereochemistry , medicinal chemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A new type of adaptive chiral thiophene‐based ligands 3 has been designed and developed. The synthetic flexibility of the thienyl ring allowed for the preparation of polydendate C2‐symmetric ligands in good yields, carrying simultaneously “hard” as well as “soft” coordinating atoms (i.e., N, S). The coordination attitude of 3 was then tested in the enantioselective base‐free Cu(OAc) 2 ‐catalyzed addition of nitromethane to aromatic aldehydes, leading to the corresponding β‐nitro alcohols in excellent yields and enantiomeric excesses up to 86%. Chirality, 2009. © 2008 Wiley‐Liss, Inc.