The Highly Enantioselective Addition of Indoles to N-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst

The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported. A total of 15 examples with product yield ranging from 89% to 99% and enantioselectivities from 90% to 97% are presented. A chiral phosphoric acid catalyst derived from a hindered binol derivative...

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Bibliographic Details
Published in:Organic letters 2007-07, Vol.9 (14), p.2609-2611
Main Authors: Rowland, Gerald B, Rowland, Emily B, Liang, Yuxue, Perman, Jason A, Antilla, Jon C
Format: Article
Language:English
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Summary:The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported. A total of 15 examples with product yield ranging from 89% to 99% and enantioselectivities from 90% to 97% are presented. A chiral phosphoric acid catalyst derived from a hindered binol derivative was employed most effectively in the reaction. Attractive features of the reaction include desirable catalyst loadings, good reactivity, generality of substrates, and easily removable groups from both nitrogen atoms.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0703579