Asymmetric alkylation of N-acylsultams: a general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives

Von Oppolzer, Wolfgang; Moretti, Robert; Thomi, Silvia Béatrice

doi:10.1016/S0040-4039(01)93810-9

Article scientifique

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Asymmetric alkylation of N-acylsultams: a general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives

Contributeurs/tricesVon Oppolzer, Wolfgang; Moretti, Robert; Thomi, Silvia Béatrice

Publié dansTetrahedron Letters, vol. 30, no. 41, p. 5603-5606

Date de publication1989

Résumé

Successive treatment of acylsultams with nBuLi or NHMDS and primary alkyl halides, followed by crystallization, gave pure C(α)-alkylation products and, via their non-destructive cleavage, enantiomerically pure alcohols or carboxylic acids. Alkylation of acylsultams 2 with primary alkyl halides gave pure 4 which was cleaved to enantiomerically pure alcohols (5) or carboxylic acids (6).

Structure d'affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (format ISO)

VON OPPOLZER, Wolfgang, MORETTI, Robert, THOMI, Silvia Béatrice. Asymmetric alkylation of N-acylsultams: a general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives. In: Tetrahedron Letters, 1989, vol. 30, n° 41, p. 5603–5606. doi: 10.1016/S0040-4039(01)93810-9

Article (Published version)

Identifiants

PID : unige:152730
DOI : 10.1016/S0040-4039(01)93810-9

URL commercialhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901938109

ISSN du journal0040-4039

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Asymmetric alkylation of N-acylsultams: a general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives

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