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Asymmetric synthesis of α‐aminophosphonic acids, I enantioselective synthesis of L‐(1‐aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation of N ‐[1‐(dimethoxyphosphoryl)ethenyl]formamide
Author(s) -
Schöllkopf Ulrich,
Hoppe Inga,
Thiele Angelika
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850316
Subject(s) - formamides , enantioselective synthesis , chemistry , formamide , catalysis , asymmetric hydrogenation , rhodium , wittig reaction , organic chemistry , medicinal chemistry
The synthesis of N ‐[bis(dimethoxyphosphoryl)methyl]formamide ( 7 ) from aminomethylene‐bis(phosphonic acid) ( 6 ) is described. 7 reacts with aldehydes in a Wittig‐Horner reaction to give N ‐[1‐(dimethoxyphosphoryl)‐1‐alkenyl]formamides 3 . From the parent compound 3a L‐(1‐amino‐ethyl)phosphonic acid ( 1 ) is obtained with e.e. ca. 76% via asymmetric catalytic hydrogenation using a rhodium catalyst in the presence of (+)‐DIOP.