Journal article
Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles
- Abstract:
- The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 2.0MB, Terms of use)
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- Publisher copy:
- 10.1039/c5cc08886k
Authors
- Publisher:
- Royal Society of Chemistry
- Journal:
- Chemical Communications More from this journal
- Volume:
- 52
- Issue:
- 4
- Pages:
- 693-696
- Publication date:
- 2015-12-01
- DOI:
- EISSN:
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1364-548X
- ISSN:
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1359-7345
- Language:
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English
- Pubs id:
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pubs:582962
- UUID:
-
uuid:11e99d37-59b7-4386-b6e3-7269b6f97ebb
- Local pid:
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pubs:582962
- Source identifiers:
-
582962
- Deposit date:
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2016-02-08
- ARK identifier:
Terms of use
- Copyright holder:
- Chintalapudi et al
- Copyright date:
- 2015
- Notes:
- This journal is © The Royal Society of Chemistry 2016. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
- Licence:
- CC Attribution (CC BY)
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