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An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst
Author(s) -
Bhadury Pinaki S.,
Zhang Yuping,
Zhang Sha,
Song Baoan,
Yang Song,
Hu Deyu,
Chen Zhuo,
Xue Wei,
Jin Linhong
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20645
Subject(s) - chemistry , cinnamaldehyde , fluorine , catalysis , trifluoromethyl , chirality (physics) , enantioselective synthesis , aldimine , enantiomer , enantiomeric excess , brønsted–lowry acid–base theory , medicinal chemistry , chiral auxiliary , organic chemistry , stereochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , alkyl
Asymmetric addition of dialkyl phosphites (CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 (CH 2 ) 3 CH 3 , CH 2 CH 2 OCH 3 and CH 2 CH 2 OC 2 H 5 ) induced by chiral organocatalyst e.g. ( R )‐ and ( S )‐3,3′‐[3,5‐bis(trifluoromethyl)phenyl] 2 ‐1,1′‐binaphthyl phosphate on fluorinated aldimines derived from cinnamaldehyde has been found effective to give new bioactive α‐aminophosphonates in good yields (58–73%) and high enantiomeric excess (64.6%–90.6%) under mild conditions. Chirality, 2009. © 2008 Wiley‐Liss, Inc.