Resolution of Terminal 1,2-Diols via Silyl Transfer

Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of...

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Published in:Journal of organic chemistry 2013-10, Vol.78 (20), p.10494-10499
Main Authors: Sun, Xixi, Worthy, Amanda D, Tan, Kian L
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Molecular Structure
Silanes - chemistry
Stereoisomerism
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description Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of chemically differentiating a terminal 1,2-diol with concomitant resolution of the enantiomers.
doi_str_mv 10.1021/jo4012909
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alcohols - chemistry
Catalysis
Molecular Structure
Silanes - chemistry
Stereoisomerism
title Resolution of Terminal 1,2-Diols via Silyl Transfer
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