Literature DB >> 29775301

Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Xinxin Shao1, Kangnan Li1, Steven J Malcolmson1.   

Abstract

Here we report highly efficient and chemoselective azadiene-imine reductive couplings catalyzed by (Ph-BPE)Cu-H that afford anti-1,2-diamines. In all cases, reactions take place with either aldimine or ketimine electrophiles to deliver a single diastereomer of product in >95:5 er. The products' diamines are easily differentiable, facilitating downstream synthesis.

Entities:  

Mesh：

Substances：

Year:  2018        PMID： 29775301      PMCID： PMC5999589          DOI： 10.1021/jacs.8b04750

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


  81 in total

1.  N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.

Authors:  Daniel L Silverio; Peng Fu; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Tetrahedron Lett       Date:  2015-04-09       Impact factor: 2.415

2.  Highly enantioselective thiourea-catalyzed nitro-Mannich reactions.

Authors:  Tehshik P Yoon; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

3.  Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl aziridines with imido carboxylates.

Authors:  Barry M Trost; Daniel R Fandrick; Tobias Brodmann; Dylan T Stiles
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors:  Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-23       Impact factor: 15.336

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  Ruthenium(II)-catalyzed regioselective reductive coupling of α-imino esters with dienes.

Authors:  Shujie Zhu; Xiaoxia Lu; Yueting Luo; Wei Zhang; Huanfeng Jiang; Ming Yan; Wei Zeng
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

7.  The fluorenone imines of glycine esters and their phosphonic acid analogues.

Authors:  Shū Kobayashi; Ryo Yazaki; Kazutaka Seki; Yasuhiro Yamashita
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

9.  Enantioselective palladium-catalyzed diamination of alkenes using N-fluorobenzenesulfonimide.

Authors:  Erica L Ingalls; Paul A Sibbald; Werner Kaminsky; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

10.  Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution.

Authors:  Daniel J Sprague; Anand Singh; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825
View more
  19 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

3.  Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Authors:  Chibueze I Onyeagusi; Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

4.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

5.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

6.  CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence.

Authors:  Yuxuan Ye; Seoung-Tae Kim; Jinhoon Jeong; Mu-Hyun Baik; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-02-20       Impact factor: 15.419

7.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

8.  Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Authors:  Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

9.  Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Xi-Jie Dai; Stephen L Buchwald
Journal:  Org Lett       Date:  2019-05-17       Impact factor: 6.005

10.  Catalytic, Enantioselective syn-Diamination of Alkenes.

Authors:  Zhonglin Tao; Bradley B Gilbert; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2019-11-19       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.