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Asymmetric Syntheses of α‐Aminophosphonic Acids, V. Synthesis of Enantiomerically Pure Diethyl 2‐Pyrrolidinyl‐ and 5‐Oxo‐2‐pyrrolidinylphosphonates
Author(s) -
Groth Ulrich,
Richter Lutz,
Schöllkopf Ulrich
Publication year - 1992
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.1992199201150
Subject(s) - chemistry , pyroglutamic acid , camphor , hydrolysis , derivative (finance) , proline , organic chemistry , medicinal chemistry , stereochemistry , amino acid , biochemistry , financial economics , economics
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.