Highly stereoselective intramolecular alpha-arylation of self-stabilized non-racemic enolates: synthesis of alpha-quaternary alpha-amino acid derivatives.
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.
Lupi
Vittoria
V
Dipartimento di Chimica Organica e Industriale, Università degli Studi, Via Venezian 21, I-20133 Milano, Italy.
Penso
Michele
M
Foschi
Francesca
F
Gassa
Federico
F
Mihali
Voichiţa
V
Tagliabue
Aaron
A
D000477:Alkylating Agents / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D000477:Alkylating Agents; D000596:Amino Acids; D004952:Esters; D013450:Sulfones; D010293:Pargyline; C458239:propargyl bromide