I. Coldham et al., PREPARATION OF BETA-AMINO ALCOHOLS BY CARBON-CARBON BOND FORMATION USING SUBSTITUTED LITHIOMETHYLPYRROLIDINES, Journal of the Chemical Society. Perkin transactions. I, (10), 1997, pp. 1481-1485
N-Thiomethylation or stannylmethylation of prolinol derivatives, follo
wed by sulfur-lithium or tin-lithium exchange is used for the formatio
n of alpha-amino-organolithiums. Condensation with aldehydes gives bet
a-amino alcohols in good yield but modest diastereoselectivity.