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

F. Foschi;
2009-01-01

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.
2009
bifunctional asymmetric catalysis; chiral nonracemic enolate; phase-transfer catalysis; enantioselective synthesis; recent progress; ammonium-salts; rearrangement; alkylation; esters; sulfamidation
Lupi, V.; Penso, M.; Foschi, F.; Gassa, F.; Mihali, V.; Tagliabue, A.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2086296
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