Literature DB >> 27275598

Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction.

Aurélien Tap1, Aurélie Blond1, Vijay N Wakchaure1, Benjamin List2.   

Abstract

Herein we describe the development of a catalytic enantioselective alkynylogous Mukaiyama aldol reaction. The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio-, diastereo-, and enantioselectivity. Our process tolerates a broad range of aldehydes in combination with diverse alkynyl-substituted ketene acetals. The reaction products can be readily derivatized to furnish a variety of highly substituted enantiomerically enriched building blocks.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acids; aldol reactions; allenes; disulfonimides; organocatalysis

Year:  2016        PMID: 27275598     DOI: 10.1002/anie.201603649

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


  13 in total

1.  Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

Authors:  Yao Jiang; Abdallah B Diagne; Regan J Thomson; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2017-01-25       Impact factor: 15.419

2.  Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.

Authors:  Krishna Yadavalli; Salvatore D Lepore
Journal:  Lett Org Chem       Date:  2022-02-01       Impact factor: 0.797

3.  Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.

Authors:  Susovan Jana; Animesh Roy; Salvatore D Lepore
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

4.  Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Authors:  Chunyin Law; Elton Kativhu; Johnny Wang; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-15       Impact factor: 15.336

5.  Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

Authors:  Deyun Qian; LinLin Wu; Zhenyang Lin; Jianwei Sun
Journal:  Nat Commun       Date:  2017-09-18       Impact factor: 14.919

6.  Coarctate and Möbius: The Helical Orbitals of Allene and Other Cumulenes.

Authors:  Marc H Garner; Roald Hoffmann; Sten Rettrup; Gemma C Solomon
Journal:  ACS Cent Sci       Date:  2018-04-25       Impact factor: 14.553

7.  Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.

Authors:  Liela Bayeh-Romero; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

8.  Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers.

Authors:  Samantha L Maki; Pradip Maity; Shannon Dougherty; Jennifer Johns; Salvatore D Lepore
Journal:  Org Lett       Date:  2019-09-16       Impact factor: 6.072

9.  Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.

Authors:  Roly J Armstrong; Meganathan Nandakumar; Rafael M P Dias; Adam Noble; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-30       Impact factor: 15.336

10.  Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes.

Authors:  Shihua Song; Jing Zhou; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2019-01-31       Impact factor: 14.919

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