Generation of aziridinyllithiums from sulfinylaziridines with tert- butyllithium: Properties, reactivity, and application to a synthesis of α,α-dialkylamino acid esters and amides including an optically active form

Tetrahedron

Volumn 56, Issue 26, 2000, Pages 4415-4425

  Satoh, Tsuyoshi ^a   Ozawa, Masaki ^a   Takano, Koji ^a   Chyouma, Tosio ^a   Okawa, Akihiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Aziridinyllithiums; Sulfinylaziridines; Sulfoxide lithium exchange; , dialkylamino acid esters

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; CHLOROFORMIC ACID ETHYL ESTER; ESTER DERIVATIVE; ISOCYANIC ACID DERIVATIVE; LITHIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESULFURIZATION; HYDROGENATION; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0034705509     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00375-6     Document Type: Article

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46. As reported in the lit. 6e, the sulfinylaziridines were synthesized starting from 1-chloroalkyl p-tolyl sulfoxides and imines. The lithium carbanions of the 1-chloroalkyl p-tolyl sulfoxides react with N-aryl aldimines, derived from arylamines and aryl aldehydes, in high yields; however, they do not react with N-alkyl aldimines, derived from alkylamines and aryl aldehydes or alkyl aldehydes. The synthesis of various kinds of the sulfinylaziridines other than those reported in this paper requires another synthetic method, which is now investigated in these laboratories.