title: A synthetic study of chiral α-hydroxy-H-phosphinates based on proline catalysis.
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.
authors.affiliation: State 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.
authors.forename: Qiuli
authors.initials: Q
authors.lastname: Yao
authors.forename: Chengye
authors.initials: C
authors.lastname: Yuan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D063065:Organophosphonates; D010721:Phosphinic Acids; C116609:3-hydroxybutanal; D011392:Proline