Literature DB >> 21275427

Facial selectivity and stereospecificity in the (4 + 3) cycloaddition of epoxy enol silanes.

Brian Lo1, Pauline Chiu.   

Abstract

The scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.

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Year:  2011        PMID： 21275427     DOI： 10.1021/ol102897d

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


  2 in total

1.  Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.

Authors:  Yunfei Du; Elizabeth H Krenske; Jennifer E Antoline; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Org Chem       Date:  2012-07-31       Impact factor: 4.354

2.  Concerted Ring Opening and Cycloaddition of Chiral Epoxy Enolsilanes with Dienes.

Authors:  Elizabeth H Krenske; Sarah Lam; Jerome P L Ng; Brian Lo; Sze Kui Lam; Pauline Chiu; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-07       Impact factor: 15.336
  2 in total

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