GAMMA-SUBSTITUTED PYRROLE-BASED SILYL DIENOL ETHERS AS ALPHA-AMINO-ACID ENOLATE EQUIVALENTS - A VERSATILE ENTRY TO RACEMIC ALPHA-SUBSTITUTED ALPHA-AMINO-ACIDS

Authors
ZANARDI F BATTISTINI L RASSU G CORNIA M CASIRAGHI G
Citation
F. Zanardi et al., GAMMA-SUBSTITUTED PYRROLE-BASED SILYL DIENOL ETHERS AS ALPHA-AMINO-ACID ENOLATE EQUIVALENTS - A VERSATILE ENTRY TO RACEMIC ALPHA-SUBSTITUTED ALPHA-AMINO-ACIDS, Journal of the Chemical Society. Perkin transactions. I, (19), 1995, pp. 2471-2475
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
19
Year of publication
1995
Pages
2471 - 2475
Database
ISI
SICI code
0300-922X(1995):19<2471:GPSDEA>2.0.ZU;2-5
Abstract
gamma-Substituted siloxypyrrole derivatives 5-7 have been synthesized by direct alkylation of utoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyr role 1. These underwent subsequent alkylation with alkyl halides or al dehydes to produce gamma,gamma-disubstituted alpha,beta-unsaturated la ctam intermediates in good yields. Oxidative cleavage of the C(3)-C(4) bond within the lactam moiety gave rise to a number of alpha-substitu ted alpha-amino acids. These include racemic alpha-methylphenylalanine 14, alpha-benzylphenylalanine 15, alpha-benzylserine 18 and alpha-met hylthreonine 21.