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Synlett 2017; 28(17): 2267-2271
DOI: 10.1055/s-0036-1590831
DOI: 10.1055/s-0036-1590831
letter
Regio- and Diastereoselective Samarium-Mediated Allylic Benzoate Reductions
Financial support from the National Science Foundation (CHE-1151492) is gratefully acknowledged.Further Information
Publication History
Received: 01 June 2017
Accepted after revision: 19 June 2017
Publication Date:
20 July 2017 (online)
Abstract
A regio- and diastereoselective samarium(II)-mediated reduction of allylic benzoates is described. Yields for the reactions are generally high with diastereoselectivities up to 90:10 and in some cases only a single regioisomer was obtained. The stereoselectivity of the reaction is proposed to arise from chelation of a hydroxyl-stereocenter and starting alkene geometry, with protonation occurring intramolecularly by samarium-bound water.
Key words
samarium - reduction - stereoselective synthesis - regioselectivity - diastereoselectivitySupporting Information
- Supporting informations for this article is available online at https://doi.org/10.1055/s-0036-1590831.
- Supporting Information
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References and Notes
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