Literature DB >> 23319206

Catalytic asymmetric synthesis of allylic alcohols and derivatives and their applications in organic synthesis.

Alexandre Lumbroso1, Michael L Cooke, Bernhard Breit.   

Abstract

Allylic alcohols represent an important and highly versatile class of chiral building blocks for organic synthesis. This Review summarizes the plethora of methods developed for the catalytic asymmetric synthesis of enantioenriched allylic alcohols. These include: dynamic kinetic resolution (DKR/DKAT), nucleophilic 1,2-addition to carbonyl groups, allylic substitution, oxidation of C-H bonds, the addition of O nucleophiles to π systems, reduction of unsaturated carbonyl compounds, and an alternative route from enantioenriched propargylic alcohols. Furthermore, these catalytic asymmetric processes are exemplified by their applications in the syntheses of complex molecules such as natural products and potential therapeutic agents.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2013        PMID: 23319206     DOI: 10.1002/anie.201204579

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


  24 in total

1.  A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

2.  Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.

Authors:  Tyler J Mann; Alexander W H Speed; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

3.  Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

Authors:  Zachary C Litman; Ankit Sharma; John F Hartwig
Journal:  ACS Catal       Date:  2017-01-30       Impact factor: 13.084

4.  Asymmetric synthesis of aryl/vinyl alkyl carbinol esters via Ni-catalyzed reductive arylation/vinylation of 1-chloro-1-alkanol esters.

Authors:  Deli Sun; Xianghua Tao; Guobin Ma; Jifen Wang; Yunrong Chen
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

5.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

6.  Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.

Authors:  Adam B Weinstein; David P Schuman; Zhi Xu Tan; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

7.  General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols.

Authors:  Marvin Parasram; Padon Chuentragool; Yang Wang; Yi Shi; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2017-10-12       Impact factor: 15.419

8.  Distal Allylic/Benzylic C-H Functionalization of Silyl Ethers Using Donor/Acceptor Rhodium(II) Carbenes.

Authors:  Janakiram Vaitla; Yannick T Boni; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-12       Impact factor: 15.336

9.  Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

Authors:  Jianyu Xu; Olivia P Bercher; Michael R Talley; Mary P Watson
Journal:  ACS Catal       Date:  2021-01-19       Impact factor: 13.084

10.  Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism.

Authors:  Yang Gao; David E Hill; Wei Hao; Brendon J McNicholas; Julien C Vantourout; Ryan G Hadt; Sarah E Reisman; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2021-06-15       Impact factor: 16.383

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