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A New Versatile Synthesis of Ring‐Substituted 2‐Cyclopropylglycines and Related Amino Acids
Author(s) -
Wessjohann Ludger,
Krass Norbert,
Yu Dahai,
Meijere Armin De
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250418
Subject(s) - chemistry , azide , nucleophile , glycine , ring (chemistry) , alkyl , salt (chemistry) , amino acid , combinatorial chemistry , catalysis , nucleophilic substitution , sodium azide , organic chemistry , biochemistry
Alkyl 2‐chloro‐2‐cyclopropylideneacetates 2 serve as universal starting materials for a new general synthesis of cyclopro‐pylglycines by a simple three‐ to four‐step methodology. 1,4‐Addition of nucleophiles, substitution with azide ion, and mild catalytic deprotection lead to a variety of salt‐free cyclopropyl‐substituted amino acids in good yields, including the natural products 2‐(1‐methylcyclopropyl)glycine ( 4 ) and cleonin ( 5 ).