Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.
Chemistry
; 15(13): 3204-20, 2009.
Article
en En
| MEDLINE
| ID: mdl-19204962
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.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Sulfonas
/
Compuestos de Vinilo
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Técnicas Químicas Combinatorias
/
Aldehídos
/
Organofosfonatos
Idioma:
En
Año:
2009
Tipo del documento:
Article