Tetrahedron

CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers

K Kitaori, Y Furukawa, H Yoshimoto, J Otera

Index: Kitaori, Kazuhiro; Furukawa, Yoshiro; Yoshimoto, Hiroshi; Otera, Junzo Tetrahedron, 1999 , vol. 55, # 50 p. 14381 - 14390

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Citation Number: 53

Abstract

The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1, 2- epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.