Literature DB >> 11975541

Unusual regioselective intramolecular Diels-Alder reaction forming tricyclo[4.3.1.0(3,7)]decane system.

Kiyosei Takasu1, Sayaka Mizutani, Masataka Ihara.   

Abstract

The intramoleculae Diels-Alder reaction of cyclohexenone having an unsaturated ester side chain afforded tricyclo[4.3.1.0(3,7)]decanone in both a regio- and stereoselective manner under TMSCl-NEt(3)-ZnBr(2) conditions. Unexpectedly, the regiochemical control was against the conventional orbital requirement.

Entities:  

Year:  2002        PMID: 11975541     DOI: 10.1021/jo016129o

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Dynamic effects on the periselectivity, rate, isotope effects, and mechanism of cycloadditions of ketenes with cyclopentadiene.

Authors:  Bryson R Ussing; Chao Hang; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

2.  Control elements in dynamically determined selectivity on a bifurcating surface.

Authors:  Jacqueline B Thomas; Jack R Waas; Michael Harmata; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419

  2 in total

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