Literature DB >> 26961497

Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Farid W van der Mei1, Hiroshi Miyamoto1, Daniel L Silverio1, Amir H Hoveyda2.   

Abstract

Catalytic allylboron additions to aldimines are presented for which small amounts of Zn(OMe)2 serve as the co-catalyst to accelerate allyl exchange and 1,3-borotropic shift processes. Low-yielding and moderately α- and diastereoselective reactions are thus turned into highly efficient γ-, diastereo-, and enantioselective transformations that exhibit considerable scope.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; borotropic shift; diastereoselective synthesis; enantioselective catalysis; homoallylic amines

Mesh：

Substances：

Year:  2016        PMID： 26961497      PMCID： PMC4973465          DOI： 10.1002/anie.201600546

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  38 in total

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2.  Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst.

Authors:  Kian L Tan; Eric N Jacobsen
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3.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

Authors:  Hao Wang; Pankaj Jain; Jon C Antilla; K N Houk
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4.  Catalytic Approach for the Formation of Optically Active Allyl alpha-Amino Acids by Addition of Allylic Metal Compounds to alpha-Imino Esters.

Authors:  Xiangming Fang; Mogens Johannsen; Sulan Yao; Nicholas Gathergood; Rita G. Hazell; Karl Anker Jørgensen
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5.  Catalytic, enantioselective alkylation of alpha-imino esters: the synthesis of nonnatural alpha-amino acid derivatives.

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Journal:  J Am Chem Soc       Date:  2002-01-09       Impact factor: 15.419

6.  Asymmetric allylation, crotylation, and cinnamylation of N-heteroaryl hydrazones.

Authors:  Miriam Inbar Feske; Alexander Buitrago Santanilla; James L Leighton
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

7.  Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters.

Authors:  Jack L-Y Chen; Helen K Scott; Matthew J Hesse; Christine L Willis; Varinder K Aggarwal
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8.  Enantioselective rhodium-catalyzed nucleophilic allylation of cyclic imines with allylboron reagents.

Authors:  Yunfei Luo; Hamish B Hepburn; Nawasit Chotsaeng; Hon Wai Lam
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  14 in total

1.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

2.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
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3.  Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl-B(pin) Compounds to Ketones and α-Ketoesters.

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4.  Versatile Homoallylic Boronates by Chemo-, SN 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution.

Authors:  Jaehee Lee; Sebastian Torker; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-20       Impact factor: 15.336

5.  Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

Authors:  Yao Jiang; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-04       Impact factor: 15.336

6.  Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.

Authors:  Farid W van der Mei; Changming Qin; Ryan J Morrison; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2017-06-24       Impact factor: 15.419

7.  Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones.

Authors:  Nicholas W Mszar; Malte S Mikus; Sebastian Torker; Fredrik Haeffner; Amir H Hoveyda
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8.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

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9.  Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NH2 -Amines by Reactions Facilitated by a Threonine-Based Boron-Containing Catalyst.

Authors:  Diana C Fager; Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

10.  γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.

Authors:  Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-01       Impact factor: 15.336
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