Literature DB >> 30160825

Enantioselective Intramolecular Copper-Catalyzed Borylacylation.

Andrew Whyte1, Katherine I Burton1, Jingli Zhang1,2, Mark Lautens1.   

Abstract

An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon-boron bond provides a platform for a wide array of diversification.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; boron; copper; cyclizations; heterocycles

Year:  2018        PMID: 30160825     DOI: 10.1002/anie.201808460

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


  12 in total

1.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

2.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

3.  Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand.

Authors:  Linglin Wu; Olga Zatolochnaya; Bo Qu; Ling Wu; Lucille A Wells; Marisa C Kozlowski; Chris H Senanayake; Jinhua J Song; Yongda Zhang
Journal:  Org Lett       Date:  2019-10-24       Impact factor: 6.005

4.  Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes.

Authors:  Xianqing Wu; Aneta Turlik; Baixue Luan; Feng He; Jingping Qu; K N Houk; Yifeng Chen
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-25       Impact factor: 16.823

5.  Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes.

Authors:  Xiangqing Jia; Ziyan Zhang; Vladimir Gevorgyan
Journal:  ACS Catal       Date:  2021-10-15       Impact factor: 13.700

6.  Three-Component Ni-Catalyzed Silylacylation of Alkenes.

Authors:  Dongshun Ni; M Kevin Brown
Journal:  ACS Catal       Date:  2021-01-26       Impact factor: 13.700

Review 7.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

8.  Synthesis of dihydroisoquinolinone-4-methylboronic esters via domino Heck/borylation using a structurally characterized palladacycle as a catalyst.

Authors:  Jhansi Rani Morla; Dastagiri Reddy Nareddula
Journal:  RSC Adv       Date:  2022-02-28       Impact factor: 3.361

9.  Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence.

Authors:  Yuanqi Wu; Lizuo Wu; Zhan-Ming Zhang; Bing Xu; Yu Liu; Junliang Zhang
Journal:  Chem Sci       Date:  2022-01-22       Impact factor: 9.825

10.  Enantio- and diastereoselective conjugate borylation/Mannich cyclization.

Authors:  Egor M Larin; Joachim Loup; Iuliia Polishchuk; Rachel J Ross; Andrew Whyte; Mark Lautens
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.