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Synthesis of Enantiomerically Pure (1 S ,2 S )‐1‐Aminocyclopropanephosphonic Acids from (2 S )‐Methylcyclopropanone Acetal
Author(s) -
Fadel Antoine,
Tesson Nicolas
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:11<2153::aid-ejoc2153>3.0.co;2-x
Subject(s) - chemistry , acetal , phosphonate , hydrogenolysis , hydrolysis , enantiomer , yield (engineering) , organic chemistry , catalysis , enantiomeric excess , enantioselective synthesis , materials science , metallurgy
A one‐pot reaction of methylcyclopropanone acetal (2 S )‐ 4b with chiral amines and a trialkyl phosphite has been devised, by means of which the amino phosphonate esters 8 are obtained with excellent diastereoselectivities. Catalytic hydrogenolysis and hydrolysis of these phosphonates gives (1 S ,2 S )‐1‐amino‐2‐methylcyclopropanephosphonic acid 1b in good overall yield and with excellent enantiomeric excess.