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

DOI: 10.1016/S0040-4020(99)00896-0

Source and publish data:

Tetrahedron p. 14381 - 14390 (1999)

Update date:2022-07-30

Topics:

Authors:

Kitaori, Kazuhiro

Furukawa, Yoshiro

Yoshimoto, Hiroshi

Otera, Junzo

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Article abstract of DOI:10.1016/S0040-4020(99)00896-0

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.

Full text of DOI:10.1016/S0040-4020(99)00896-0

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