NDLI: Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.

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Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.

Content Provider	Semantic Scholar
Author	Mosse, Sarah Sulzer‐ Alexakis, Alexandre Mareda, Jiri Bollot, Guillaume Bernardinelli, Gérald Filinchuk, Yaroslav
Copyright Year	2009
Abstract	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 gamma-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.
File Format	PDF HTM / HTML
DOI	10.1002/chem.200801892
PubMed reference number	19204962
Journal	Medline
Volume Number	15
Issue Number	13
Alternate Webpage(s)	http://filinchuk.com/publ/FilArt85.pdf
Alternate Webpage(s)	https://doi.org/10.1002/chem.200801892
Journal	Chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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