Modular Access to the Stereoisomers of Fused Bicyclic Azepines: Rhodium-Catalyzed Intramolecular Stereospecific Hetero-[5+2] Cycloaddition of Vinyl Aziridines and Alkenes
The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stere...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 52; pp. 15854 - 15858 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
21.12.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 |
| DOI | 10.1002/anie.201509185 |
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| Abstract | The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high‐yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Z geometry of the CC bonds in the vinyl aziridine‐alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered.
E/Z access: The title reaction was realized and a range of chiral fused bicyclic azepines bearing multiple contiguous stereogenic centers can be obtained in a high‐yielding and stereoselective manner. The E/Z geometry of the CC bonds in the substrates affect the stereochemistry of the cycloadducts and up to six stereoisomers can be obtained. |
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| AbstractList | The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high‐yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Z geometry of the CC bonds in the vinyl aziridine‐alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. The first rhodium-catalyzed intramolecular hetero-[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high-yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Zgeometry of the CC bonds in the vinyl aziridine-alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high‐yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E / Z geometry of the CC bonds in the vinyl aziridine‐alkene substrates impact the cis / trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. The first rhodium-catalyzed intramolecular hetero-[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high-yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Z geometry of the C=C bonds in the vinyl aziridine-alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high‐yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Z geometry of the CC bonds in the vinyl aziridine‐alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. E/Z access: The title reaction was realized and a range of chiral fused bicyclic azepines bearing multiple contiguous stereogenic centers can be obtained in a high‐yielding and stereoselective manner. The E/Z geometry of the CC bonds in the substrates affect the stereochemistry of the cycloadducts and up to six stereoisomers can be obtained. |
| Author | Feng, Jian-Jun Lin, Tao-Yan Wu, Hai-Hong Zhang, Junliang |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26555739$$D View this record in MEDLINE/PubMed |
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| Keywords | chirality RING EXPANSIONS REACTIVITY VINYLCYCLOPROPANES ALKYNES ALLENES SUBSTITUTED CYCLOPROPANES cycloaddition stereoselectivity heterocycles 7-MEMBERED RINGS METAL ASYMMETRIC TOTAL-SYNTHESIS SELECTIVITY rhodium |
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| Snippet | The first rhodium‐catalyzed intramolecular hetero‐[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal... The first rhodium-catalyzed intramolecular hetero-[5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal... |
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| SubjectTerms | Alkenes Chemistry Chemistry, Multidisciplinary chirality Cycloaddition heterocycles Physical Sciences Rhodium Science & Technology Stereochemistry Stereoisomerism Stereoisomers Stereoselectivity Substrates |
| Title | Modular Access to the Stereoisomers of Fused Bicyclic Azepines: Rhodium-Catalyzed Intramolecular Stereospecific Hetero-[5+2] Cycloaddition of Vinyl Aziridines and Alkenes |
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