Stereoselective Michael additions of lithiated ortho -sulfinylbenzyl carbanions derived from α-amino nitriles.

Enantiomerically pure α -substituted α -aminoortho-sulfinylphenylacetonitriles have been readily prepared by the reaction of diastereoisomeric mixtures of α -amino phenylacetonitriles with differently sized cycloalkenones and 2-methyl cyclopentenone in the presence of lithium bases. The reactions proceeded with high levels of stereoselectivity, generating molecules containing up to three asymmetric carbon centers in just one synthetic step. [ABSTRACT FROM AUTHOR]