Journal of Organic Chemistry p. 2321 - 2327 (1983)
Update date:2022-08-04
Topics:
Grunewald, Gary L.
Paradkar, Vidyadhar M.
Pazhenchevsky, Bharak
Pleiss, Michael A.
Sall, Daniel J.
et al.
The synthesis of 5-, 6-, 7-, and 8-(trifluoromethyl)benzonorbornen-2-yl alcohols 6a-9a (exo) and 11a-14a (endo) and an examination of the stereospecificity of the conversion to amines via phthalimides are reported.The exo alcohols were prepared from 5-(trifluoromethyl)benzonorbornadiene (16) and 6-(trifluoromethyl)benzonorbornadiene (23) by hydroboration-oxidation.The endo alcohols were available from the corresponding exo alcohols by oxidation to the benzonorbornen-2-ones 24 (5-CF3), 25 (6-CF3), 26 (7-CF3), and 27 (8-CF3) followed by diborane reduction.While in the presence of the electron-withdrawing CF3 group the exo alcohols gave predominantly the endo amines, the endo alcohols afforded exclusively the exo amines.
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Doi:10.1055/s-1982-29747
(1982)Doi:10.1021/jacs.6b07172
(2016)Doi:10.1007/BF00568946
(1982)Doi:10.1002/anie.200461301
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(1982)