Intermolecular Regio‐ and Stereoselective Hetero‐[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines
We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐ and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide....
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 3; pp. 887 - 891 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
14.01.2019
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐ and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide. This new reaction provides quick access to highly substituted nitrogen‐containing seven‐membered rings—azepanes. Notably, a broad range of oxidopyrylium ylides and cyclic imines participate in this novel hetero‐[5+2] cycloaddition reaction and the cycloadducts can be readily transformed into the core skeletons of bioactive natural products. DFT calculations revealed that the cycloaddition proceeds through a stepwise pathway and the imine nitrogen atom serves as the nucleophile to initiate the cycloaddition.
Step by step: A hetero‐[5+2] cycloaddition of oxidopyrylium ylides and cyclic imines has been realized. This method provides efficient access to highly substituted azepane scaffolds. DFT calculations indicate that a stepwise mechanism is favored over a concerted one. |
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| AbstractList | We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐ and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide. This new reaction provides quick access to highly substituted nitrogen‐containing seven‐membered rings—azepanes. Notably, a broad range of oxidopyrylium ylides and cyclic imines participate in this novel hetero‐[5+2] cycloaddition reaction and the cycloadducts can be readily transformed into the core skeletons of bioactive natural products. DFT calculations revealed that the cycloaddition proceeds through a stepwise pathway and the imine nitrogen atom serves as the nucleophile to initiate the cycloaddition.
Step by step: A hetero‐[5+2] cycloaddition of oxidopyrylium ylides and cyclic imines has been realized. This method provides efficient access to highly substituted azepane scaffolds. DFT calculations indicate that a stepwise mechanism is favored over a concerted one. We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐ and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide. This new reaction provides quick access to highly substituted nitrogen‐containing seven‐membered rings—azepanes. Notably, a broad range of oxidopyrylium ylides and cyclic imines participate in this novel hetero‐[5+2] cycloaddition reaction and the cycloadducts can be readily transformed into the core skeletons of bioactive natural products. DFT calculations revealed that the cycloaddition proceeds through a stepwise pathway and the imine nitrogen atom serves as the nucleophile to initiate the cycloaddition. |
| Author | Zhao, Changgui Glazier, Daniel A. Yin, Dan Tang, Weiping Yang, Daoshan Liu, Peng Guzei, IIia A. Aristov, Michael M. |
| Author_xml | – sequence: 1 givenname: Changgui surname: Zhao fullname: Zhao, Changgui organization: University of Wisconsin-Madison – sequence: 2 givenname: Daniel A. surname: Glazier fullname: Glazier, Daniel A. organization: University of Wisconsin-Madison – sequence: 3 givenname: Daoshan surname: Yang fullname: Yang, Daoshan organization: Qingdao University of Science and Technology – sequence: 4 givenname: Dan surname: Yin fullname: Yin, Dan organization: University of Wisconsin-Madison – sequence: 5 givenname: IIia A. surname: Guzei fullname: Guzei, IIia A. organization: University of Wisconsin-Madison – sequence: 6 givenname: Michael M. surname: Aristov fullname: Aristov, Michael M. organization: University of Wisconsin-Madison – sequence: 7 givenname: Peng surname: Liu fullname: Liu, Peng email: pengliu@pitt.edu organization: University of Pittsburgh – sequence: 8 givenname: Weiping orcidid: 0000-0002-0039-3196 surname: Tang fullname: Tang, Weiping email: weiping.tang@wisc.edu organization: University of Wisconsin-Madison |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30476368$$D View this record in MEDLINE/PubMed |
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| Keywords | VINYL AZIRIDINES azepanes oxidoprylium ylide imines ALKYNES [5+2] cycloaddition heterocycles RING 3-ACYLOXY-1,4-ENYNES CHIRALITY ACCESS INTRAMOLECULAR 5+2 CYCLOADDITION ALKALOIDS |
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| Snippet | We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐... We have developed the first intermolecular hetero-[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio-... |
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| SubjectTerms | [5+2] cycloaddition azepanes Chemistry Chemistry, Multidisciplinary Cycloaddition heterocycles Imines Natural products Nitrogen oxidoprylium ylide Physical Sciences Science & Technology Stereochemistry Stereoselectivity Substitution reactions |
| Title | Intermolecular Regio‐ and Stereoselective Hetero‐[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines |
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