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Asymmetric Copper‐Catalyzed Vinylogous Mukaiyama Michael Addition of Cyclic Dienol Silanes to Unsaturated α‐Keto Phosphonates
Author(s) -
Steinkamp AnneDorothee,
Frings Marcus,
Thomé Isabelle,
Schiffers Ingo,
Bolm Carsten
Publication year - 2015
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.201500861
Subject(s) - stereocenter , nucleophile , electrophile , stereoselectivity , chemistry , phosphonate , catalysis , copper , aldol reaction , silanes , ligand (biochemistry) , organic chemistry , medicinal chemistry , enantioselective synthesis , silane , biochemistry , receptor
A highly stereoselective vinylogous Mukaiyama Michael reaction (VMMR) leading to α‐keto phosphonate‐containing γ‐butenolides with two stereogenic centers is described. The presented transformation is catalyzed by a combination of a commercially available C 2 ‐symmetric bisoxazoline (BOX) ligand and a copper salt and tolerates a variety of nucleophiles and electrophiles. The stereoselectivities of the reactions are good to excellent and the products are obtained in moderate to high yields.