Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2- cyclopentenones

Singh, Gurpreet; Meyer, Angelica Michelle; Aubé, Jeffrey

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Issue Date

2014-01-03

Author

Singh, Gurpreet

Meyer, Angelica Michelle

Aubé, Jeffrey

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 the Journal of Organic Chemistry, 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/jo402539p.

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Abstract

Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.

Citation

Singh, G., Meyer, A., & Aubé, J. (2014). Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones. The Journal of Organic Chemistry, 79(1), 452–458. http://doi.org/10.1021/jo402539p

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