Article

Allenyl azide cycloaddition chemistry. 2,3-cyclopentennelated indole synthesis through indolidene intermediates.

Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
The Journal of Organic Chemistry (impact factor: 4.45). 06/2009; 74(14):4958-74. DOI:10.1021/jo900659w pp.4958-74
Source: PubMed

ABSTRACT The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the hnu/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.

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Keywords

2,3-cyclopentennelated indole products
 
Computational studies
 
copper present
 
hnu/CuI conditions
 
indolidene intermediates
 
multistep reaction support
 
photochemical
 
photochemical/CuI-mediated cascade cyclizations
 
reactions
 
regioselectivity
 
regioselectivity branch point