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A Synthetic Study of Chiral α‐Hydroxy‐ H ‐Phosphinates Based on Proline Catalysis
Author(s) -
Yao Qiuli,
Yuan Chengye
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204195
Subject(s) - diastereomer , enantioselective synthesis , proline , chemistry , chirality (physics) , acetone , aldol reaction , catalysis , stereochemistry , phosphorus , organic chemistry , amino acid , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
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.