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A general synthesis of dendralenes.
George, Josemon; Ward, Jas S; Sherburn, Michael S.
Afiliação
  • George J; Research School of Chemistry , Australian National University , Canberra , ACT 2601 , Australia . Email: michael.sherburn@anu.edu.au.
  • Ward JS; Research School of Chemistry , Australian National University , Canberra , ACT 2601 , Australia . Email: michael.sherburn@anu.edu.au.
  • Sherburn MS; Research School of Chemistry , Australian National University , Canberra , ACT 2601 , Australia . Email: michael.sherburn@anu.edu.au.
Chem Sci ; 10(43): 9969-9973, 2019 Nov 21.
Article em En | MEDLINE | ID: mdl-32055353
ABSTRACT
The first general synthetic approach to substituted [3]- and higher dendralenes is reported. Fifty-one mono- through to penta-substituted dendralenes carrying alkyl-, cycloalkyl-, alkenyl-, alkynyl-, aryl- and heteroaryl-substitutents are accessed, and the first (E)/(Z)-stereoselective syntheses of dendralenes are reported (twenty-eight examples). The approach involves twofold Pd(0)-catalyzed Negishi couplings of 1,1-dibromoalkenes with alkenylzinc reagents, and exploits both substrate- and catalyst-controlled aspects of chemo-, regio- and stereoselectivity in the two C(sp2)-C(sp2) bond forming steps. The value of the new hydrocarbons in rapid structural complexity generation is demonstrated through their deployment in unprecedented diene- and triene-transmissive pericyclic reaction sequences.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article