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Asymmetric Syntheses of α-Aminophosphonic Acids, V. Synthesis of Enantiomerically Pure Diethyl 2-Pyrrolidinyl- and 5-Oxo-2-pyrrolidinylphosphonates

✍ Scribed by Groth, Ulrich ;Richter, Lutz ;Schöllkopf, Ulrich

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 791 KB
Volume: 1992
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1992199201150

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✦ Synopsis

Abstract

Enantiomerically pure 3‐ and 4‐substituted phosphonic acid derivatives 5 of pyroglutamic acid were prepared by a Michael addition of the lithiated (+)‐camphor derivative 2 to α,β‐unsaturated esters and subsequent hydrolysis. The reduction of the lactams 5 with LiBH~4~/BF~3~ · OEt~2~ afforded substituted phosphonic acid analogues 7 of proline.

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