Stereospecific ring expansion of chiral vinyl aziridines

Matthew Brichacek; Mauricio Navarro Villalobos; Alexandra Plichta; Jon T. Njardarson

doi:10.1021/ol200263g

Stereospecific ring expansion of chiral vinyl aziridines

Matthew Brichacek, Mauricio Navarro Villalobos, Alexandra Plichta, Jon T. Njardarson

Chemistry and Biochemistry

Research output: Contribution to journal › Article

50 Scopus citations

Abstract

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis-or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.(Figure Presented)

Original language	English (US)
Pages (from-to)	1110-1113
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/ol200263g
State	Published - Mar 4 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200263g

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Brichacek, M., Navarro Villalobos, M., Plichta, A., & Njardarson, J. T. (2011). Stereospecific ring expansion of chiral vinyl aziridines. Organic Letters, 13(5), 1110-1113. https://doi.org/10.1021/ol200263g

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