Work

Phosphine-Promoted [3 + 3] Annulations of Aziridines With Allenoates: Facile Entry Into Highly Functionalized Tetrahydropyridines

Year: 2009

Type: article

Abstract: The phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactions, run under very mild conditions, for the preparation of highly functionalized tetrahydropyridines in yields of up to 98% and trans/cis ratios of up to 97:3. In addition to steps that are typical of nucleophilic phosphine-catalyzed reactions of allenoates, the mechanism of this new reaction features apparent nucleophilic aromatic substitution and concomitant desulfonylation, processes hitherto unknown during phosphine-promoted cycloaddition reactions. Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja8097349

Authors: Hongchao Guo, Qihai Xu, Ohyun Kwon

Institution: University of California, Los Angeles

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Pilot-Scale Library Production Based on Phosphine Catalysis of Allenes, Phosphine-Catalyzed Annulations and their Applications