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Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors
Author(s) -
SulzerMossé Sarah,
Alexakis Alexandre,
Mareda Jiri,
Bollot Guillaume,
Bernardinelli Gerald,
Filinchuk Yaroslav
Publication year - 2009
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.200801892
Subject(s) - enantioselective synthesis , pyrrolidine , conjugate , michael reaction , sulfonyl , chemistry , enantiomer , organic chemistry , organocatalysis , combinatorial chemistry , catalysis , mathematics , mathematical analysis , alkyl
Chiral framework : Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.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.