Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Literature DB >> 33755457

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Colton R Davis¹, Irungu K Luvaga¹, Joseph M Ready¹.

Abstract

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Entities: Chemical

Mesh：

Substances：

Year: 2021 PMID： 33755457 PMCID： PMC8459435 DOI： 10.1021/jacs.1c01242

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

52 in total

1. Catalytic three-component coupling of alkynes, imines, and organoboron reagents.

Authors: Sejal J Patel; Timothy F Jamison
Journal: Angew Chem Int Ed Engl Date: 2003-03-28 Impact factor: 15.336

2. Multicomponent Reactions with Isocyanides.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-15 Impact factor: 15.336

3. Selection of boron reagents for Suzuki-Miyaura coupling.

Authors: Alastair J J Lennox; Guy C Lloyd-Jones
Journal: Chem Soc Rev Date: 2013-10-03 Impact factor: 54.564

4. Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds.

Authors: Josep Llaveria; Daniele Leonori; Varinder K Aggarwal
Journal: J Am Chem Soc Date: 2015-08-21 Impact factor: 15.419

5. Synthesis and Utility of Dihydropyridine Boronic Esters.

Authors: Santanu Panda; Aaron Coffin; Q Nhu Nguyen; Dean J Tantillo; Joseph M Ready
Journal: Angew Chem Int Ed Engl Date: 2015-12-22 Impact factor: 15.336

6. Iridium-Catalyzed Asymmetric Synthesis of Functionally Rich Molecules Enabled by (Phosphoramidite,Olefin) Ligands.

Authors: Simon L Rössler; David A Petrone; Erick M Carreira
Journal: Acc Chem Res Date: 2019-06-19 Impact factor: 22.384

7. Boronic esters in asymmetric synthesis.

Authors: Donald S Matteson
Journal: J Org Chem Date: 2013-08-14 Impact factor: 4.354

8. Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters.

Authors: Santanu Panda; Joseph M Ready
Journal: J Am Chem Soc Date: 2018-10-05 Impact factor: 15.419

9. Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Authors: Chunyin Law; Elton Kativhu; Johnny Wang; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2020-04-15 Impact factor: 15.336

10. Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles.

Authors: Xiao Zhang; Wen-Bo Liu; Hang-Fei Tu; Shu-Li You
Journal: Chem Sci Date: 2015-06-08 Impact factor: 9.825

4 in total