Literature DB >> 30020777

Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.

James M Cabrera1, Johannes Tauber1, Wandi Zhang1, Ming Xiang1, Michael J Krische1.   

Abstract

Enantioselectivity increases with increasing carbonyl electrophilicity in 2-propanol-mediated reductive couplings of aldehydes with branched aryl-substituted allylic acetates to form products of carbonyl anti-(α-aryl)allylation. This unusual phenomenon is caused by aldehyde coordination to diastereomeric kinetic vs thermodynamic carbonyl binding sites that deliver enantiomeric products. Exploiting this effect, anti-diastereo- and enantioselective (α-aryl)allylations of fluoral hydrate and difluoroacetaldehyde ethyl hemiacetal were developed.

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Year:  2018        PMID： 30020777      PMCID： PMC6206506          DOI： 10.1021/jacs.8b05725

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


  42 in total

1.  Enantioselective catalytic allylation of carbonyl groups by umpolung of pi-allyl palladium complexes.

Authors:  Giuseppe Zanoni; Serafino Gladiali; Alberto Marchetti; Paolo Piccinini; Ilenia Tredici; Giovanni Vidari
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-06       Impact factor: 15.336

Review 2.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

3.  Catalytic asymmetric fluorination comes of age.

Authors:  Vincent A Brunet; David O'Hagan
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

Authors:  Tomoya Miura; Yui Nishida; Masao Morimoto; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

Review 5.  Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions.

Authors:  Xiu-Hua Xu; Kohei Matsuzaki; Norio Shibata
Journal:  Chem Rev       Date:  2014-08-14       Impact factor: 60.622

6.  Cross-metathesis/isomerization/allylboration sequence for a diastereoselective synthesis of anti-homoallylic alcohols from allylbenzene derivatives and aldehydes.

Authors:  Rémy Hemelaere; François Carreaux; Bertrand Carboni
Journal:  Chemistry       Date:  2014-09-11       Impact factor: 5.236

7.  Catalytic nucleophilic 'umpoled' π-allyl reagents.

Authors:  Kim Spielmann; Gilles Niel; Renata Marcia de Figueiredo; Jean-Marc Campagne
Journal:  Chem Soc Rev       Date:  2018-02-19       Impact factor: 54.564

8.  Catalytic Asymmetric Synthesis of Tertiary Alcohols and Oxetenes Bearing a Difluoromethyl Group.

Authors:  Kohsuke Aikawa; Seiya Yoshida; Daisuke Kondo; Yuya Asai; Koichi Mikami
Journal:  Org Lett       Date:  2015-09-30       Impact factor: 6.005

9.  Organocatalytic asymmetric Strecker reaction of di- and trifluoromethyl ketoimines. Remarkable fluorine effect.

Authors:  Yun-Lin Liu; Tao-Da Shi; Feng Zhou; Xiao-Li Zhao; Xin Wang; Jian Zhou
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

10.  Formation of chiral fluoroalkyl products through copper-free enantioselective allylic alkylation catalyzed by an NHC ligand.

Authors:  David Grassi; Hailing Li; Alexandre Alexakis
Journal:  Chem Commun (Camb)       Date:  2012-10-19       Impact factor: 6.222
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  3 in total

1.  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

2.  Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl anti-(α-Aryl)allylation.

Authors:  Ming Xiang; Ankan Ghosh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

3.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  3 in total

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