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.
Highly stereoselective intramolecular α-arylation of self-stabilized non-racemic enolates : synthesis of α-quaternary α-amino acid derivatives / V. Lupi, M. Penso, F. Foschi, F. Gassa, V. Mihali, A. Tagliabue. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 2009:33(2009 Jul 13), pp. 5012-5014. [10.1039/b910326k]
Highly stereoselective intramolecular α-arylation of self-stabilized non-racemic enolates : synthesis of α-quaternary α-amino acid derivatives
V. LupiPrimo
;F. Foschi;F. Gassa;V. MihaliPenultimo
;A. TagliabueUltimo
2009
Abstract
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.Pubblicazioni consigliate
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