Literature DB >> 29376366

A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Erica Y Tsai1, Richard Y Liu1, Yang Yang1, Stephen L Buchwald1.   

Abstract

We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and sensitive functional groups are efficiently coupled with high stereoselectivity and exclusive branched regioselectivity. In stoichiometric experiments, each elementary step of the proposed hydrocupration-addition-metathesis mechanism can be followed by NMR spectroscopy.

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Year:  2018        PMID： 29376366      PMCID： PMC5821421          DOI： 10.1021/jacs.7b12271

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  80 in total

1.  Allylsilane-vinylarene cross-metathesis enables a powerful approach to enantioselective imine allylation.

Authors:  John D Huber; Nicholas R Perl; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  In situ catalytic generation of allylcopper species for asymmetric allylation: toward 1H-isochromene skeletons.

Authors:  Junya Kawai; Prasanna Kumara Chikkade; Yohei Shimizu; Motomu Kanai
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-03       Impact factor: 15.336

3.  Hydroaminomethylation Beyond Carbonylation: Allene-Imine Reductive Coupling by Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Susumu Oda; Brannon Sam; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

4.  Balancing C=C Functionalization and C=O Reduction in Cu-H Catalysis.

Authors:  Jens Mohr; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-04       Impact factor: 15.336

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

7.  A general catalytic allylation using allyltrimethoxysilane.

Authors:  Shingo Yamasaki; Kunihiko Fujii; Reiko Wada; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

8.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

9.  The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.

Authors:  Lutz F Tietze; Tom Kinzel; C Christian Brazel
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.

Authors:  KyungA Lee; Daniel L Silverio; Sebastian Torker; Daniel W Robbins; Fredrik Haeffner; Farid W van der Mei; Amir H Hoveyda
Journal:  Nat Chem       Date:  2016-05-23       Impact factor: 24.427
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  31 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

3.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

4.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

5.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

6.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

7.  Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

Authors:  Youming Huang; Sebastian Torker; Xinghan Li; Juan Del Pozo; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-06       Impact factor: 15.336

8.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

9.  Copper-Catalyzed Enantioselective Hydroamination of Alkenes.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Organic Synth       Date:  2018

10.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419
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