Literature DB >> 15624970

A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.

Kerrie L Burgess1, Neil J Lajkiewicz, Amitav Sanyal, Wanlin Yan, John K Snyder.   

Abstract

(-)-(R)-9-(1,2-Dimethoxyethyl)anthracene (8) is successfully employed as a chiral template in the Diels-Alder/retro-Diels-Alder sequence for the preparation of alpha,beta-unsaturated lactams. The cycloadditions proceed with complete diastereoselectivity, and regioselectivity in subsequent transformations of the carbonyl groups is also excellent. Flash vacuum pyrolysis accomplishes the cycloreversion.

Entities:  

Year:  2005        PMID: 15624970     DOI: 10.1021/ol047968a

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


  2 in total

1.  Enantioselective syntheses of candenatenins B and C using a chiral anthracene auxiliary.

Authors:  Amanda L Jones; Xiang Liu; John K Snyder
Journal:  Tetrahedron Lett       Date:  2010-02-17       Impact factor: 2.415

2.  Diels-Alder Reactivity of a Chiral Anthracene Template with Symmetrical and Unsymmetrical Dienophiles: A DFT Study.

Authors:  Jennifer P Hernández-Mancera; Francisco Núñez-Zarur; Ricardo Vivas-Reyes
Journal:  ChemistryOpen       Date:  2020-07-10       Impact factor: 2.911

  2 in total

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