Abstract
A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.
| Original language | English |
|---|---|
| Pages (from-to) | 167-190 |
| Number of pages | 24 |
| Journal | Arkivoc |
| Volume | 2007 |
| Issue number | 5 |
| Publication status | Published - 2007 |
| Externally published | Yes |
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Keywords
- Asymmetric synthesis
- Cycloadditions
- Debenzylation
- High pressure
- Sulfur heterocycles
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides. / Rogachev, Victor O.; Metz, Peter.
In: Arkivoc, Vol. 2007, No. 5, 2007, p. 167-190.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides
AU - Rogachev, Victor O.
AU - Metz, Peter
PY - 2007
Y1 - 2007
N2 - A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.
AB - A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.
KW - Asymmetric synthesis
KW - Cycloadditions
KW - Debenzylation
KW - High pressure
KW - Sulfur heterocycles
UR - http://www.scopus.com/inward/record.url?scp=33846243270&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33846243270&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:33846243270
VL - 2007
SP - 167
EP - 190
JO - Arkivoc
JF - Arkivoc
SN - 1424-6376
IS - 5
ER -