Conformationally constrained dipeptides. Obtention of enantiomerically pure 6‐acetamido‐5‐oxo‐1,2,3,5,6,7‐hexahydro‐3‐indolizine carboxylic acid | Zendy

Millet Régis | Zendy; Meulon Emmanuelle | Zendy; Goossens Laurence | Zendy; Houssin Raymond | Zendy; Hénichart JeanPierre | Zendy; Rigo Benoît | Zendy

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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.

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