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.
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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DOI：
10.1021/ol034455f
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发表时间：
2003-04
期刊：
影响因子：
5.2
通讯作者：
M. Sasaki;K. Tanino;Atsushi Hirai;M. Miyashita
中科院分区：
文献类型：
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作者：
M. Sasaki;K. Tanino;Atsushi Hirai;M. Miyashita
采用NaN(3)-(CH(3)O)(3)B、NaSPh-(CH(3)O)(3)B或NaCN-(C(2)H(5)O)(3)B体系，制备了2,3-环氧醇与亲核试剂的高效C2选择性取代反应。该反应是通过硼螯合物分子内环氧化物的新开孔进行的，这是由实验和量子力学研究提出的。
[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.