Base-Mediated Regio- and Stereoselective Intermolecular Addition of Alkynes to N-Heterocycles

The regio- and stereoselective addition of N-heterocycles to alkynes using KOH is reported. Formation of (Z)-isomers and their conversion to (E)-products were found to be dependent upon time as well as the choice of base. Selective attack of N-heterocycles on a more electrophilic alkynyl carbon was...

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Bibliographic Details
Published in:Organic letters 2011-04, Vol.13 (7), p.1630-1633
Main Authors: Verma, Akhilesh Kumar, Joshi, Megha, Singh, Ved Prakash
Format: Article
Language:English
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Summary:The regio- and stereoselective addition of N-heterocycles to alkynes using KOH is reported. Formation of (Z)-isomers and their conversion to (E)-products were found to be dependent upon time as well as the choice of base. Selective attack of N-heterocycles on a more electrophilic alkynyl carbon was supported by DFT calculations, and the stereochemistry of the products was established by X-ray crystallographic studies and intramolecular cyclization of ortho-haloalkynes in indolo-[2,1-a]isoquinolines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200048z