Literature DB >> 22235777

Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.

Gregory R Boyce1, Shubin Liu, Jeffrey S Johnson.   

Abstract

The three-component coupling of Mg acetylides, silyl glyoxylates, and nitroalkenes results in a highly diastereoselective Kuwajima-Reich/vinylogous Michael cascade that provides tetrasubstituted silyloxyallene products. The regio- and diastereoselectivity were studied using DFT calculations. These silyloxyallenes were converted to cyclopentenols and cyclopentitols via a unique Lewis acid assisted Henry cyclization. The alkene functionality present in the cyclopentanol products can be elaborated using diastereoselective ketohydroxylation reactions.
© 2012 American Chemical Society

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Year:  2012        PMID： 22235777      PMCID： PMC3265386          DOI： 10.1021/ol2033527

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

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Authors: 
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6.  The structure of pactamycin.

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