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 |
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| Authors: | Sasaki Minoru Tanino Keiji Hirai Atsushi Miyashita Masaaki |
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| Affiliation: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. |
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| 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. |
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