Conjugate Additions to Alkylidene Bis(Sulfoxides) (pages 1825–1833)
Dr. Franck Brebion, Dr. Guillaume Vincent, Dr. Saloua Chelli, Dr. Ophélie Kwasnieski, Dr. Francisco Najera, Dr. Bénédicte Delouvrié, Prof. Ilan Marek, Dr. Etienne Derat, Dr. Jean-Philippe Goddard, Prof. Max Malacria and Prof. Louis Fensterbank
Article first published online: 11 MAR 2011 | DOI: 10.1002/asia.201000904
Taking the Michael: Alkylidene bis(sulfoxides) are exquisite Michael acceptors toward a broad series of nucleophiles, and in most cases the reaction affords the adducts in high yields with complete diastereoselectivity. Copper reagents are also good nucleophiles in this reaction, but proceed with an inversion in stereoselectivity. Rationalization was provided by DFT calculations.