Literature DB >> 25111443

Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling.

James Y Hamilton1, Nicole Hauser, David Sarlah, Erick M Carreira.   

Abstract

An enantioselective allyl-allylsilane cross-coupling involving racemic branched allylic alcohols and allylsilanes is reported. An iridium-(P,olefin) phosphoramidite complex enables the transformation with high regio- and stereoselectivity under operationally simple conditions. The utility of the coupling is demonstrated in a concise catalytic, enantioselective synthesis of a pyrethroid insecticide protrifenbute.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,5-diene; allylic substitution; allylsilane; enantioselectivity; iridium

Year:  2014        PMID: 25111443     DOI: 10.1002/anie.201406077

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: The role of ligands.

Authors:  Michael J Ardolino; James P Morken
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

2.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

3.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

4.  A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes.

Authors:  Ding-Wei Ji; Yan-Cheng Hu; Hao Zheng; Chao-Yang Zhao; Qing-An Chen; Vy M Dong
Journal:  Chem Sci       Date:  2019-05-16       Impact factor: 9.825

5.  Enantioselective and site-specific copper-catalyzed reductive allyl-allyl cross-coupling of allenes.

Authors:  Guoxing Xu; Bin Fu; Haiyan Zhao; Yanfei Li; Ge Zhang; Ying Wang; Tao Xiong; Qian Zhang
Journal:  Chem Sci       Date:  2018-12-04       Impact factor: 9.825

6.  Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans.

Authors:  Emeline Rideau; Stephen P Fletcher
Journal:  Beilstein J Org Chem       Date:  2015-12-03       Impact factor: 2.883

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.