Literature DB >> 29272124

2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Kangnan Li1, Xinxin Shao1, Luke Tseng1, Steven J Malcolmson1.   

Abstract

We introduce a new strategy for synthesis of chiral amines: couplings of α-aminoalkyl nucleophiles generated by enantioselective migratory insertion of 2-azadienes to a Cu-H. In this report, we demonstrate its application in catalytic reductive coupling of 2-azadienes and ketones to furnish 1,2-amino tertiary alcohols with vicinal stereogenic centers.

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Year:  2018        PMID： 29272124      PMCID： PMC5936605          DOI： 10.1021/jacs.7b12213

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


  59 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.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

3.  Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines.

Authors:  Leonardus H Leijendekker; Jens Weweler; Tobias M Leuther; Jan Streuff
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-26       Impact factor: 15.336

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

Authors:  Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

5.  Metallaphotoredox-catalysed sp(3)-sp(3) cross-coupling of carboxylic acids with alkyl halides.

Authors:  Craig P Johnston; Russell T Smith; Simon Allmendinger; David W C MacMillan
Journal:  Nature       Date:  2016-08-17       Impact factor: 49.962

6.  Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis.

Authors:  Candice L Joe; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

7.  Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors:  Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419

8.  Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.

Authors:  C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-10-09       Impact factor: 15.419

9.  Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates.

Authors:  Barry M Trost; Xiaoxun Li
Journal:  Chem Sci       Date:  2017-08-15       Impact factor: 9.825

10.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419
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  21 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.  Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors:  Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

Review 10.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622
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