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Enantioselective synthesis of α‐aminophosphonic acid derivatives by hydrogenation
Author(s) -
Schmidt Ute,
Krause Hans Walter,
Oehme Günther,
Michalik Manfred,
Fischer Christine
Publication year - 1998
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/(sici)1520-636x(1998)10:7<564::aid-chir3>3.0.co;2-2
Subject(s) - chemistry , enantioselective synthesis , chirality (physics) , enantiomer , catalysis , asymmetric hydrogenation , enantiomeric excess , organic chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Chiral α‐aminophosphonic acid derivatives are efficiently synthesized by asymmetric hydrogenation of the prochiral N ‐acyl‐α,β‐dehydroaminophosphonates. PROPRAPHOS‐Rh‐catalysts from readily available ( S )‐ and ( R )‐Propranolol proved to be suitable in the homogenous reaction affording an enantiomeric excess of 87–92% with high rate. The aminophosphonic acid derivatives and precursors were fully characterized by 1 H, 13 C, and 31 P NMR spectroscopy. Chirality 10:564–572, 1998. © 1998 Wiley‐Liss, Inc.