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.

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

V. Lupi;F. Foschi;GASSA, FEDERICO;V. Mihali;A. Tagliabue
2009-07-13

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.
bifunctional asymmetric catalysis ; chiral nonracemic enolate ; phase-transfer catalysis ; enantioselective synthesis ; recent progress ; ammonium-salts ; rearrangement ; alkylation ; esters ; sulfamidation
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/68562
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