Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 13, Pages 3204-3220Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801892
Keywords
aldehydes; amines; asymmetric synthesis; Michael addition; organocatalysis
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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.
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