Literature DB >> 26637131

Asymmetric Allylic Alkylation of β-Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst.

Yusuke Kita1, Rahul D Kavthe1, Hiroaki Oda1, Kazushi Mashima2.   

Abstract

Asymmetric allylic alkylation of β-ketoesters with allylic alcohols catalyzed by [Ni(cod)2]/(S)-H8-BINAP was found to be a superior synthetic protocol for constructing quaternary chiral centers at the α-position of β-ketoesters. The reaction proceeded in high yield and with high enantioselectivity using various β-ketoesters and allylic alcohols, without any additional activators. The versatility of this methodology for accessing useful and enantioenriched products was demonstrated.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkylation; allylic compounds; asymmetric catalysis; enantioselectivity; nickel

Year:  2015        PMID： 26637131     DOI： 10.1002/anie.201508757

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


  9 in total

1.  Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, and N-Heterocycles.

Authors:  Ciarán C Lynch; Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2020-04-07       Impact factor: 6.005

2.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

3.  Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

Authors:  Trevor D Lohrey; Alexander Q Cusumano; William A Goddard; Brian M Stoltz
Journal:  ACS Catal       Date:  2021-08-02       Impact factor: 13.700

Review 4.  Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts.

Authors:  Lars Süsse; Brian M Stoltz
Journal:  Chem Rev       Date:  2021-02-11       Impact factor: 60.622

5.  Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols.

Authors:  Hua Zhang; Xiao-Yu Zhan; Yu Dong; Jian Yang; Shuai He; Zhi-Chuan Shi; Xiao-Mei Zhang; Ji-Yu Wang
Journal:  RSC Adv       Date:  2020-04-30       Impact factor: 4.036

6.  Enantioselective Nickel-Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization.

Authors:  Connor Yap; Gabriel M J Lenagh-Snow; Somnath Narayan Karad; William Lewis; Louis J Diorazio; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-12       Impact factor: 15.336

7.  Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols.

Authors:  Xue-Gong Jia; Peng Guo; Jicheng Duan; Xing-Zhong Shu
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825

8.  Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Authors:  Aurapat Ngamnithiporn; Carina I Jette; Shoshana Bachman; Scott C Virgil; Brian M Stoltz
Journal:  Chem Sci       Date:  2018-01-24       Impact factor: 9.825

9.  Case Study of N-i Pr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2 ].

Authors:  Lukas Tendera; Moritz Helm; Mirjam J Krahfuss; Maximilian W Kuntze-Fechner; Udo Radius
Journal:  Chemistry       Date:  2021-11-16       Impact factor: 5.020
  9 in total

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