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Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.

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.

SUBMITTER: Shinde AH

PROVIDER: S-EPMC10119688 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.

Shinde Anand H AH Thomas Annu Anna AA Mague Joel T JT Sathyamoorthi Shyam S

The Journal of organic chemistry 20211019 21

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 fo ...[more]

PMID: 34665630

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