Literature DB >> 19663466

Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.

Gregory K Friestad1, Hye Jin Lee.   

Abstract

Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl(4) produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon nucleophiles.

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Year:  2009        PMID： 19663466     DOI： 10.1021/ol901613k

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


  3 in total

1.  Participation of alkoxy groups in reactions of acetals: violation of the reactivity/selectivity principle in a Curtin-Hammett kinetic scenario.

Authors:  Angie Garcia; Jillian R Sanzone; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-19       Impact factor: 15.336

2.  Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects.

Authors:  Vi Tuong Tran; K A Woerpel
Journal:  J Org Chem       Date:  2013-06-24       Impact factor: 4.354

3.  Oxo-Rhenium-Mediated Allylation of Furanoside Derivatives: A Computational Study on the Mechanism and the Stereoselectivity.

Authors:  Emanuele Casali; Alessio Porta; Lucio Toma; Giuseppe Zanoni
Journal:  J Org Chem       Date:  2022-07-12       Impact factor: 4.198
  3 in total

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