Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 14, Pages 4958-4974Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900659w
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Funding
- National Institutes of Health
- General Medical Sciences division [GM72572]
- National Science Foundation [0131112]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0131112] Funding Source: National Science Foundation
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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 hv/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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