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Reduction of halohydrins, halohydrin esters, and epoxides

Chiral halohydrins epoxides.1 The esters (2) of the chiral alcohol 1 derived from camphor-10-sulfonic acid, are converted to a-chloro esters (3) by O-silylation and reaction with NCS with high diastereoselectivity. Reduction of 3 with Ca(BH4)2 results in the recovered auxiliary and the chlorohydrin 4 with clean retention. Cyclization of 4 to the terminal epoxide 5 proceeds with clean inversion. [Pg.62]

See other pages where Reduction of halohydrins, halohydrin esters, and epoxides is mentioned: [Pg.341] [Pg.440] [Pg.341] [Pg.440] [Pg.607] [Pg.607] [Pg.292] [Pg.607] [Pg.607] [Pg.607] [Pg.580] [Pg.341] [Pg.440] [Pg.17]

See also in sourсe #XX -- [ Pg.341 ]

See also in sourсe #XX -- [ Pg.341 ]

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Epoxides reduction

Esters epoxidation

Esters reduction

Halohydrin

Halohydrins

Halohydrins reduction

Reduction of epoxide

Reduction of epoxides

Reduction of esters