Section 54
Chapter 53,561

Highly stereoselective intramolecular alpha-arylation of self-stabilized non-racemic enolates: synthesis of alpha-quaternary alpha-amino acid derivatives

Lupi, V.; Penso, M.; Foschi, F.; Gassa, F.; Mihali, V.ţa.; Tagliabue, A.

Chemical Communications 33: 5012-5014


ISSN/ISBN: 1364-548X
PMID: 19668833
DOI: 10.1039/b910326k
Accession: 053560023

The 'one-pot' stereoselective conversion of N-(4-nitrobenzene)sulfonyl-alpha-amino acid tert-butyl esters into the corresponding N-alkyl-alpha-(4-nitrophenyl)-alpha-amino esters has been realized through N-alkylation of the starting amido esters, followed by N-C(alpha) migration of the p-nitrophenyl group and the loss of sulfur dioxide; the asymmetric induction is determined by an intermediate non-racemic enolate, without the need of an external source of chirality.

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