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 | |
| State | Published - Mar 4 2011 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Stereospecific ring expansion of chiral vinyl aziridines. / Brichacek, Matthew; Navarro Villalobos, Mauricio; Plichta, Alexandra; Njardarson, Jon T.
In: Organic Letters, Vol. 13, No. 5, 04.03.2011, p. 1110-1113.Research output: Contribution to journal › Article
}
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)
UR - http://www.scopus.com/inward/record.url?scp=79952173211&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79952173211&partnerID=8YFLogxK
U2 - 10.1021/ol200263g
DO - 10.1021/ol200263g
M3 - Article
C2 - 21309528
AN - SCOPUS:79952173211
VL - 13
SP - 1110
EP - 1113
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 5
ER -