Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles

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 diastereoselec...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (4), p.693-696
Main Authors: Chintalapudi, V, Galvin, E A, Greenaway, R L, Anderson, E A
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Cycloaddition
Facial
Isomerization
Selectivity
Synthesis
Tethering
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08886k