Synlett

Synthesis of β-Amino Alcohols via the Reduction of Lactamides Derived from Ethyl (2S)-Lactate with Borane-Methyl Sulfide

FW Lewis, MC Eichler, DH Grayson

Index: Lewis, Frank W.; Eichler, Matthias C.; Grayson, David H. Synlett, 2009 , # 12 p. 1923 - 1928

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Citation Number: 3

Abstract

Brown and co-workers have shown that the rates of reduction of amides, esters, and nitriles with borane-methyl sulfide can be significantly increased by the distillation of dimethyl sulfide from the reaction mixture and by employing boron trifluoride etherate as Lewis acid. [¹6] We were thus attracted to the possibility of employing this reagent combination for the synthesis of enantiopure β-amino alcohols 9 from lactamides 8, as borane-methyl sulfide is more convenient to ...