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Updated: May 13, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
A synthetic study of chiral α-hydroxy-H-phosphinates based on proline catalysis
1State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, PR China.
Abstract:
A highly enantioselective synthesis of α-hydroxyphosphinates was achieved based on the L-proline-catalyzed aldol reaction of α-acylphosphinates and acetone. Due to the preexisting chirality at the phosphorus center, mixtures of two diastereomers of the α-hydroxyphosphinates were obtained in moderate to good yields, with simultaneously high enantioselectivity for both diastereomers. The products could be converted into α-hydroxy-H-phosphinates with satisfactory yields. Furthermore, an unprecedented oxidation-reduction reaction of the α-hydroxyphosphinates or α-hydroxy-H-phosphinates to form phosphonates was observed, and the mechanism involved in such a chemical transformation is discussed.
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