Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/11851
Title: Highly enantioselective conjugate additions of phosphites to alpha,beta-unsaturated N-Acylpyrroles and Imines : a practical approach to enantiomerically enriched amino phosphonates
Authors: Zhao, D
Wang, Y
Mao, L
Wang, R
Keywords: Asymmetric catalysis
Hydrophosphonylation
Michael addition
Phosphonates
Synthetic methods
Issue Date: 2009
Publisher: Wiley-VCH
Source: Chemistry - a European journal, 2009, v. 15, no. 41, p. 10983-10987 How to cite?
Journal: Chemistry - a European journal 
Abstract: The first highly enantioselective phosphonylation of alpha,beta-unsaturated N-acylpyrroles has been developed. Excellent yields (91-99%) and enantioselectivities (up to >99% enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N-acylpyrroles under mild conditions. In particular, when diethyl phosphite was employed to test the scope of the N-acylpyrroles, almost optically pure products (98 to > 99 % ee) were obtained for 20 examples of N-acylpyrroles. Moreover, optically pure alpha-substituted beta- or gamma-amino phosphonates can be obtained by several simple transformations of the pyrrolyl phosphonates. The versatility of the N-acylpyrrole moiety makes the phosphorus adducts powerful chiral building blocks that enable the synthesis of various phosphonate-containing compounds. Finally, the present strategy can also be applied to the asymmetric hydrophosphonylation of N-acylimines with high enantioselectivities (93 to > 99 % ee).
URI: http://hdl.handle.net/10397/11851
ISSN: 0947-6539
EISSN: 1521-3765
DOI: 10.1002/chem.200901901
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