Organic Chemistry

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.

Content

Thumbnail image of Manuscript for submission.pdf

Supplementary material

Thumbnail image of JTM1417_0m_a.txt
JTM1417 0m a
Thumbnail image of SI for submission.pdf
SI for submission