N-silyl protecting groups for labile aziridines: application toward the synthesis of N-H aziridinomitosenes

Don L Warner; Amber M Hibberd; Monica Kalman; Artis Klapars; Edwin Vedejs

doi:10.1021/jo7013615

N-silyl protecting groups for labile aziridines: application toward the synthesis of N-H aziridinomitosenes

J Org Chem. 2007 Oct 26;72(22):8519-22. doi: 10.1021/jo7013615. Epub 2007 Oct 2.

Authors

Don L Warner¹, Amber M Hibberd, Monica Kalman, Artis Klapars, Edwin Vedejs

Affiliation

¹ Department of Chemistry, Boise State University, Boise, Idaho 83725, USA. dwarner@boisestate.edu

PMID: 17910500
DOI: 10.1021/jo7013615

Abstract

Hindered N-silylamines were examined for their utility to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive aziridinomitosene framework. tert-Butyldiphenylsilyl and modified tert-butyldiphenylsilyl groups were the most resistant to nitrogen-silicon bond cleavage under various reaction conditions and were thus employed in transformations relevant to aziridinomitosene synthesis. The N-silylaziridines 7a, 21a, and 21b underwent azomethine ylide cycloaddition and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aziridines / chemical synthesis
Aziridines / chemistry*
Molecular Conformation
Stereoisomerism

Substances

Aziridines
aziridinomitosene

Abstract

Publication types

MeSH terms

Substances

Grants and funding