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Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates
Shinde, Anand H. Thomas, Annu Anna Mague, Joel T. Sathyamoorthi, Shyam
Shinde, Anand H.
Thomas, Annu Anna
Mague, Joel T.
Sathyamoorthi, Shyam
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Abstract
We present highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates. “Arming” the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity in these reactions. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The scalability of the oxidative cyclization was demonstrated, and the product cyclophosphoramidates were shown to be valuable synthons, including for tether removal. With chiral alkenyl precursors, enantiopure cyclic phosphoramidates were formed.
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This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2021 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.1c01483.
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2021-10-19
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American Chemical Society
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Shinde, A. H., Thomas, A. A., Mague, J. T., & Sathyamoorthi, S. (2021). Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates. The Journal of organic chemistry, 86(21), 14732–14758. https://doi.org/10.1021/acs.joc.1c01483