Literature DB >> 11348200

Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

F Cohen1, D W MacMillan, L E Overman, A Romero.   

Abstract

[reaction: see text]. Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

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Year:  2001        PMID： 11348200     DOI： 10.1021/ol0157003

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


  6 in total

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Authors:  Shengfei Jin; Vu T Nguyen; Hang T Dang; Dat P Nguyen; Hadi D Arman; Oleg V Larionov
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Journal:  Tetrahedron       Date:  2011-09-19       Impact factor: 2.457

4.  Origin of stereocontrol in the construction of the 12-oxatricyclo[6.3.1.0(2,7)]dodecane ring system by Prins-pinacol reactions.

Authors:  Larry E Overman; Paul S Tanis
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

5.  [2-(4-Chloro-phen-yl)-5-phenyl-oxolan-3-yl](cyclo-penten-yl)methanone.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-07

6.  Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Authors:  Zhi-Wei Jiao; Yong-Qiang Tu; Qing Zhang; Wen-Xing Liu; Shu-Yu Zhang; Shao-Hua Wang; Fu-Min Zhang; Sen Jiang
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  6 in total

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