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

Research output: Contribution to journal › Article › peer-review

63 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
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200263g

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title = "Stereospecific ring expansion of chiral vinyl aziridines",

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)",

author = "Matthew Brichacek and \{Navarro Villalobos\}, Mauricio and Alexandra Plichta and Njardarson, \{Jon T.\}",

year = "2011",

month = mar,

day = "4",

doi = "10.1021/ol200263g",

language = "English (US)",

volume = "13",

pages = "1110--1113",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Stereospecific ring expansion of chiral vinyl aziridines

AU - Brichacek, Matthew

AU - Navarro Villalobos, Mauricio

AU - Plichta, Alexandra

AU - Njardarson, Jon T.

PY - 2011/3/4

Y1 - 2011/3/4

N2 - 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)

AB - 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)

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U2 - 10.1021/ol200263g

DO - 10.1021/ol200263g

M3 - Article

C2 - 21309528

AN - SCOPUS:79952173211

SN - 1523-7060

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SP - 1110

EP - 1113

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Stereospecific ring expansion of chiral vinyl aziridines

Abstract

ASJC Scopus subject areas

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CCDC 1425101: Experimental Crystal Structure Determination

CCDC 1425100: Experimental Crystal Structure Determination

CCDC 1425103: Experimental Crystal Structure Determination

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Stereospecific ring expansion of chiral vinyl aziridines

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1425101: Experimental Crystal Structure Determination

CCDC 1425100: Experimental Crystal Structure Determination

CCDC 1425103: Experimental Crystal Structure Determination

Cite this