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Stereoselective synthesis of stable isotope‐labeled L‐α‐amino acids: enantioselective synthesis of 13 C‐, 15 N‐labeled L‐proline using Oppolzer's glycine template
Author(s) -
Lodwig Siegfried N.,
Unkefer Clifford J.
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(1998110)41:11<983::aid-jlcr152>3.0.co;2-m
Subject(s) - chemistry , proline , glycine , stereoselectivity , enantioselective synthesis , amino acid , stereochemistry , alkylation , organic chemistry , biochemistry , catalysis
We have developed a stereoselective route to the synthesis of stable isotope‐labeled L‐proline. Alkylation of (2 R )‐ N ‐{ N ′‐[bis(methylthio)methylidine]‐glycyl}bornane‐10,2‐sultam with 3‐chloro‐iodopropane yielded (2 R )‐N‐{(2′ S )‐2′‐{[ Bis (methylthio)methylidine]amino}‐5‐chloropentan‐1‐oyl}bornane‐10,2‐sultam. Cyclization to the imino acid occurred during the sequential removal of the α‐amino protecting group and the chiral auxiliary. Copyright © 1998 John Wiley & Sons, Ltd.