✦ LIBER ✦

A versatile asymmetric synthesis of α-amino α-alkyl-phosphonic acids of high enantiomeric purity

✍ Scribed by Stephen Hanessian; Youssef L. Bennani

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 312 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97092-8

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✦ Synopsis

A general protocol for the synthesis of a-amino-a-alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from (R,R)and (S,S)-1,2diaminocyclohexane. 2 CSu Br(CH&Br. 2. NaN,, DMF,140% Me Y Es& 70-75% (4) 4 h., 95%. (3) 2 Y= Cl (mp. 84°C. [aIan -109.8' c 1.0 CHCl3 3 Y= N3 (mp. 87'C. [a]% -263.8" c 1.0 CHCl3 4 ([ala, -185.2' c 1.02 CHClJ 4 1. Base, THF, -78'C 2. Rx 1N HQ w

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