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

Venukadasula, Phanindra K. M.; Chegondi, Rambabu; Suryn, Gregory M.; Hanson, Paul R.

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Issue Date

2012-05-18

Author

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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Abstract

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.

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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