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Conformationally constrained dipeptides. Obtention of enantiomerically pure 6‐acetamido‐5‐oxo‐1,2,3,5,6,7‐hexahydro‐3‐indolizine carboxylic acid
Author(s) -
Millet Régis,
Meulon Emmanuelle,
Goossens Laurence,
Houssin Raymond,
Hénichart JeanPierre,
Rigo Benoît
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370613
Subject(s) - chemistry , racemization , indolizine , bicyclic molecule , lactam , carbamate , carboxylic acid , trimethylsilyl , iodide , enantiomer , stereochemistry , cleavage (geology) , organic chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering
The separation of a stereoisomeric mixture of esters 6, and the synthesis of the new enantiomerically pure unsaturated 6,5‐fused bicyclic lactam 2 are described. The key‐step involves trimethylsilyl iodide cleavage, without racemization, of a vinylogous carbamate. The cis N‐ acetylamino acid 2 is a new scaffold for the synthesis of rigid β‐turn mimetics.