70. “Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael accepptors”
    S. Sulzer-Mossé, A. Alexakis, J. Mareda, G. Bollot, G. Bernardinelli, Y. Filinchuk
    Chem. Eur. J. 2009, 15, 3204-3220.

Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99% ee. This novel process provides synthetically useful chiral γ-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.

DOI : 10.1002/chem.200801892 

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