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Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors

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Published in Chemistry - A European Journal. 2009, vol. 15, no. 13, p. 3204-3220
Abstract 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.
Keywords AldehydesAminesAsymmetric synthesisMichael additionOrganocatalysis
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PMID: 19204962
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Deposited on : 2009-03-27

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