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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Bibliographic Details
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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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4012909