Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings

2009 ◽  
Vol 131 (46) ◽  
pp. 17024-17029 ◽  
Author(s):  
Wei Li ◽  
Ananda Herath ◽  
John Montgomery
Keyword(s):  
Reductive Couplings

scholarly journals 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

2021 ◽  
Author(s):  
Pengfei Zhou ◽  
Xinxin Shao ◽  
Steven Malcolmson
Keyword(s):  
Enantioselective Synthesis ◽  
Allylic Amines ◽  
Reductive Couplings

We introduce a new reagent class, 2-azatrienes, as a platform for catalytic enantioselective synthesis of allylic amines. Herein, we demonstrate their promise by diasteredivergent and enantioselective synthesis of <i>syn</i>- and <i>anti</i>-1,2-diamines by Cu-bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE, <i>anti</i>-diamines are obtained, and with the rarely utilized t-Bu-BDPP, <i>syn</i>-diamines are generated.<br>

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

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1253-1268 ◽  
Author(s):  
Steven J. Malcolmson ◽  
Kangnan Li ◽  
Xinxin Shao
Keyword(s):  
Organic Synthesis ◽  
Metal Species ◽  
Chiral Amines ◽  
Chiral Amine ◽  
Tertiary Alcohols ◽  
Reductive Couplings ◽  
Benzylic Amines ◽  
Important Objective ◽  
New Strategies

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.1 Introduction2 Background: Umpolung Strategies for Preparing Chiral Amines3 Background: 2-Azadienes4 Reductive Couplings of 2-Azadienes5 Fluoroarylations of gem-Difluoro-2-azadienes6 Summary and Outlook

Reductive couplings of acid chlorides mediated by SmI2

1989 ◽  
Vol 30 (52) ◽  
pp. 7407-7410 ◽  
Author(s):  
J. Collin ◽  
F. Dallemer ◽  
J.L. Namy ◽  
H.B. Kagan
Keyword(s):  
Acid Chlorides ◽  
Reductive Couplings

New N-Heterocyclic Carbene Ligand and Its Application in Asymmetric Nickel-Catalyzed Aldehyde/Alkyne Reductive Couplings.

ChemInform ◽  
2007 ◽  
Vol 38 (50) ◽  
Author(s):  
Mani Raj Chaulagain ◽  
Grant J. Sormunen ◽  
John Montgomery
Keyword(s):  
Reductive Couplings

scholarly journals ChemInform Abstract: Nickel-Catalyzed Reductive Couplings and Cyclizations

ChemInform ◽  
2011 ◽  
Vol 42 (36) ◽  
pp. no-no
Author(s):  
Hasnain A. Malik ◽  
Ryan D. Baxter ◽  
John Montgomery
Keyword(s):  
Reductive Couplings

ChemInform Abstract: Samarium Diiodide-Mediated Reductive Couplings of Chiral Nitrones with Aldehydes/Ketones and Acyl Chlorides.

ChemInform ◽  
2010 ◽  
Vol 41 (26) ◽  
pp. no-no
Author(s):  
Shao-Feng Wu ◽  
Yuan-Ping Ruan ◽  
Xiao Zheng ◽  
Pei-Qiang Huang
Keyword(s):  
Samarium Diiodide ◽  
Acyl Chlorides ◽  
Reductive Couplings

ChemInform Abstract: Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes.

ChemInform ◽  
2011 ◽  
Vol 42 (12) ◽  
pp. no-no
Author(s):  
Wei Li ◽  
Nan Chen ◽  
John Montgomery
Keyword(s):  
Reductive Couplings

Cathodic reductive couplings and hydrogenations of alkenes and alkynes catalyzed by the B12 model complex

2017 ◽  
Vol 839 ◽  
pp. 71-77 ◽  
Author(s):  
Hisashi Shimakoshi ◽  
Zhongli Luo ◽  
Kazuya Tomita ◽  
Yoshio Hisaeda
Keyword(s):  
Model Complex ◽  
Reductive Couplings
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