A Phosphate Tether-Mediated, One-pot, Sequential RCM/CM/Chemo-selective Hydrogenation Protocol

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Issue Date
2012-05-18Author
Venukadasula, Phanindra K. M.
Chegondi, Rambabu
Suryn, Gregory M.
Hanson, Paul R.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol301007h
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Show full item recordAbstract
A versatile three-step, one-pot, sequential reaction protocol involving RCM, CM, and chemoselective hydrogenation is reported. This phosphate tether-mediated process occurs without intermediate isolation, is chemoselective and is governed by stereoelectronic properties innate to phosphate tethers, which ultimately act to preserve the integrity of the bisallylic, bicyclic phosphate for subsequent nucleophilic additions. Overall, this process can be used to efficiently generate advanced polyol synthons.
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Citation
Venukadasula, P. K. M., Chegondi, R., Suryn, G. M., & Hanson, P. R. (2012). A Phosphate Tether-Mediated, One-pot, Sequential RCM/CM/Chemo-selective Hydrogenation Protocol. Organic Letters, 14(10), 2634–2637. http://doi.org/10.1021/ol301007h
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