Literature DB >> 17968865

Metal-catalyzed enantioselective allylation in asymmetric synthesis.

Zhan Lu1, Shengming Ma.   

Abstract

Metal-catalyzed enantioselective allylation, which involves the substitution of allylic metal intermediates with a diverse range of different nucleophiles or S(N)2'-type allylic substitution, leads to the formation of C-H, -C, -O, -N, -S, and other bonds with very high levels of asymmetric induction. The reaction may tolerate a broad range of functional groups and has been applied successfully to the synthesis of many natural products and new chiral compounds.

Entities:  

Year:  2008        PMID: 17968865     DOI: 10.1002/anie.200605113

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


  110 in total

1.  Direct and enantioselective {alpha}-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis.

Authors:  Anthony Mastracchio; Alexander A Warkentin; Abbas M Walji; David W C MacMillan
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-04       Impact factor: 11.205

2.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

3.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

4.  Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors:  Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

5.  Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

6.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

7.  Palladacyclic imidazoline-naphthalene complexes: synthesis and catalytic performance in Pd(II)-catalyzed enantioselective reactions of allylic trichloroacetimidates.

Authors:  Jeffrey S Cannon; James H Frederich; Larry E Overman
Journal:  J Org Chem       Date:  2012-01-30       Impact factor: 4.354

8.  "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Authors:  Joseph J Topczewski; Matthew R Porter
Journal:  Synlett       Date:  2018-07       Impact factor: 2.454

9.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

10.  Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates.

Authors:  Mitsuhiro Ueda; John F Hartwig
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

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