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Chemistry. 2013 May 3;19(19):6080-8. doi: 10.1002/chem.201204195. Epub 2013 Mar 7.

A synthetic study of chiral α-hydroxy-H-phosphinates based on proline catalysis.

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1
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.

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.

PMID:
23471759
DOI:
10.1002/chem.201204195
[Indexed for MEDLINE]
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