Preparation of β-amino alcohols by carbon–carbon bond formation using substituted lithiomethylpyrrolidines

Abstract

N-Thiomethylation or stannylmethylation of prolinol derivatives, followed by sulfur–lithium or tin–lithium exchange is used for the formation of α-amino-organolithiums. Condensation with aldehydes gives β-amino alcohols in good yield but modest diastereoselectivity.