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 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Literature DB >> 33731976

2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Steven J Malcolmson¹, Kangnan Li¹, Xinxin Shao¹.

Abstract

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.

Entities: Chemical

Keywords: 2-azadienes; amino alcohols; cross-coupling; diamines; fluoroarylation; reductive coupling

Year: 2019 PMID： 33731976 PMCID： PMC7963344 DOI： 10.1055/s-0037-1611770

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

137 in total

1. Use of nonfunctionalized enamides and enecarbamates in asymmetric synthesis.

Authors: Kovuru Gopalaiah; Henri B Kagan
Journal: Chem Rev Date: 2011-05-13 Impact factor: 60.622

2. Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO₂.

Authors: Yong-Yuan Gui; Naifu Hu; Xiao-Wang Chen; Li Li Liao; Tao Ju; Jian-Heng Ye; Zhen Zhang; Jing Li; Da-Gang Yu
Journal: J Am Chem Soc Date: 2017-11-10 Impact factor: 15.419

Review 3. Asymmetric 1,3-dipolar cycloadditions of acrylamides.

Authors: Marie Kissane; Anita R Maguire
Journal: Chem Soc Rev Date: 2009-12-07 Impact factor: 54.564

4. Transition-metal-free chemo- and regioselective vinylation of azaallyls.

Authors: Minyan Li; Osvaldo Gutierrez; Simon Berritt; Ana Pascual-Escudero; Ahmet Yeşilçimen; Xiaodong Yang; Javier Adrio; Georgia Huang; Eiko Nakamaru-Ogiso; Marisa C Kozlowski; Patrick J Walsh
Journal: Nat Chem Date: 2017-04-17 Impact factor: 24.427

1. A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors: Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2021-08-23 Impact factor: 16.383

1 in total

2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

1. Use of nonfunctionalized enamides and enecarbamates in asymmetric synthesis.

2. Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO₂.

Review 3. Asymmetric 1,3-dipolar cycloadditions of acrylamides.

4. Transition-metal-free chemo- and regioselective vinylation of azaallyls.

5. Arylation of benzyl amines with aromatic nitriles.

6. Hydroaminoalkylation of unactivated olefins with dialkylamines.

7. N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

8. Enantioselective methodologies using N-carbamoyl-imines.

9. Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes.

10. Dual catalysis for enantioselective convergent synthesis of enantiopure vicinal amino alcohols.

1. A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.