First Cobalt(I)-Catalyzed [6 + 2] Cycloadditions of Cycloheptatriene with Alkynes
- 10 May 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (12), 2353-2356
- https://doi.org/10.1021/ol050618j
Abstract
[reaction: see text] The CoI2(dppe)/Zn/ZnI2 system effectively catalyzes the [6 + 2] cycloaddition of cycloheptatriene with terminal alkynes to afford 7-alkyl-bicyclo[4.2.1]nona-2,4,7-trienes in fair to excellent yields. The catalyst proved to be tolerant toward functional groups such as ketone, sulfone, ester, ketal, ether, alcohol, imide, and nitrile. The enantioselective cycloaddition of CHT and phenylacetylene with BINOL phosphoramidite ligand 4 afforded the cycloadduct 3a (R = Ph) in 91% yield and 74% ee.Keywords
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