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 P-nitro alcohols in excellent yields and enantiomeric excesses up to 86%. Chirality 21:239-244, 2009. (c) 2008 Wiley-Liss, Inc.

New Adaptive Chiral Thiophene Ligands for Copper-Catalyzed Asymmetric Henry Reaction

CADONI, ENZO;USAI, MICHELE
2009-01-01

Abstract

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 P-nitro alcohols in excellent yields and enantiomeric excesses up to 86%. Chirality 21:239-244, 2009. (c) 2008 Wiley-Liss, Inc.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/97036
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