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Borinic Acid-catalyzed Regioselective Functionalization of Polyols

The selective manipulation of hydroxyl groups in di- and polyols is a frequently encountered problem in organic synthesis. Such processes are often tedious and/or moderate yielding, and often necessitate multistep protection / deprotection sequences. Applying boron–diol interactions previously exploited in molecular recognition and based on methods previously developed in our research group, we have developed two classes of chemical transformations:
1. Regioselective sulfonylations of carbohydrate derivatives catalyzed by a borinic ester, providing access to the corresponding mono-tosylates in high yields;
2. Selective monoalkylations and monosulfonylations of structurally diverse 1,2- and 1,3-diol substrates.

Identiferoai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/31637
Date04 January 2012
CreatorsWilliamson, Caitlin
ContributorsTaylor, Mark S.
Source SetsUniversity of Toronto
Languageen_ca
Detected LanguageEnglish
TypeThesis

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