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Literature DB >> 26458555

A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes.

Tao Jia¹, Peng Cao¹, Bing Wang¹, Yazhou Lou¹, Xuemei Yin¹, Min Wang¹, Jian Liao¹.

Abstract

A cooperative Cu/Pd-catalyzed asymmetric three-component reaction of styrenes, B2(pin)2, and allyl carbonates was reported. This reaction, in the presence of chiral CuOAc/SOP and achiral Pd(dppf)Cl2 catalysts, occurs smoothly with high enantioselectivities (up to 97% ee) . The allylboration products, which contain alkene (or diene) unite and alkylboron group, are easily functionalized. The utility of this protocol was demonstrated through the synthesis of an antipsychotic drug, (-)-preclamol.

Entities: Chemical Gene

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Year: 2015 PMID： 26458555 DOI： 10.1021/jacs.5b09146

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

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Cited

38 in total

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors: Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal: Science Date: 2016-01-01 Impact factor: 47.728

2. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors: Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-07-20 Impact factor: 15.336

3. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors: Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal: Isr J Chem Date: 2019-09-10 Impact factor: 3.333

Review 4. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors: Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal: Angew Chem Int Ed Engl Date: 2019-10-08 Impact factor: 15.336

A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes.

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

2. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

3. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Review 4. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

5. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

6. Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides.

7. Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

8. Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

9. Catalytic Enantioselective Arylboration of Alkenylarenes.

10. A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.