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Synlett 2014; 25(2): 251-254
DOI: 10.1055/s-0033-1340163
DOI: 10.1055/s-0033-1340163
letter
A Chiral Benzyl Group as a Chiral Auxiliary and Protecting Group for the Synthesis of Optically Active 1,2-Diols and (+)-Frontalin
Authors
Further Information
Publication History
Received: 22 August 2013
Accepted after revision: 30 September 2013
Publication Date:
05 November 2013 (online)
Abstract
Chelation-controlled asymmetric nucleophilic addition of a Grignard reagent to chiral α-benzyloxy ketones gives the corresponding alcohols with high diastereoselectivities (up to 96% de) by 1,4-asymmetric induction. A chiral benzyl group is used as a chiral auxiliary as well as a protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin.
Key words
nucleophilic addition - diols - α-benzyloxy ketones - (+)-frontalin - stereoselective synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
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