The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate

Minoru Sasaki; Keiji Tanino; Atsushi Hirai; Masaaki Miyashita

doi:10.1021/ol034455f

The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: the first endo-mode epoxide-opening reaction through an intramolecular metal chelate

Org Lett. 2003 May 15;5(10):1789-91. doi: 10.1021/ol034455f.

Authors

Minoru Sasaki¹, Keiji Tanino, Atsushi Hirai, Masaaki Miyashita

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

PMID: 12735778
DOI: 10.1021/ol034455f

Abstract

[reaction: see text] Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN(3)-(CH(3)O)(3)B, NaSPh-(CH(3)O)(3)B, or NaCN-(C(2)H(5)O)(3)B system. The reaction proceeds through novel endo-mode epoxide opening of an intramolecular boron chelate, which was suggested from both experimental and quantum mechanic studies.