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Chiral Guanidinium Salt Catalyzed Enantioselective Phospha‐Mannich Reactions
Author(s) -
Fu Xiao,
Loh WeiTian,
Zhang Yan,
Chen Tao,
Ma Ting,
Liu Hongjun,
Wang Jianmin,
Tan ChoonHong
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200903971
Subject(s) - enantioselective synthesis , phosphinate , phosphine , catalysis , chemistry , salt (chemistry) , nucleophile , phosphine oxide , diamine , combinatorial chemistry , mannich reaction , organic chemistry , medicinal chemistry , fire retardant
Zero, one, or two? Guanidinium catalyst 1⋅ HBAr F 4 (Ar F =3,5‐(CF 3 ) 2 C 6 H 3 , Bn=benzyl, Ts=4‐toluenesulfonyl) was obtained in a single step from a commercially available diamine. By using this catalyst an asymmetric phospha‐Mannich reaction has been developed, involving secondary phosphine oxides and H‐phosphinates as the P nucleophile. A series of enantiomerically enriched α‐amino phosphine oxides ( 2 ), α‐amino phosphinate, and H‐phosphinates containing a P‐chiral center were prepared.