Literature DB >> 24266761

Enantioselective propargylation and allenylation reactions of ketones and imines.

Hanna M Wisniewska1, Elizabeth R Jarvo.   

Abstract

Enantioselective propargylation and allenylation reactions pose an interesting challenge because they require control of regioselectivity as well as enantioselectivity. This review presents recent advances in enantioselective propargylation and allenylation reactions of ketones and imines. In this context, a brief discussion of the possible mechanisms of these transformations and consequences for regioselectivity is provided.

Entities:  

Year:  2013        PMID： 24266761     DOI： 10.1021/jo4019107

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  Catalytic, Enantioselective Synthesis of Allenyl Boronates.

Authors:  De-Wei Gao; Yiyang Xiao; Mingyu Liu; Zhen Liu; Malkanthi K Karunananda; Jason S Chen; Keary M Engle
Journal:  ACS Catal       Date:  2018-03-21       Impact factor: 13.084

2.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

3.  Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

Authors:  Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

Review 4.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

5.  Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

Authors:  Gilmar A Brito; Woo-Ok Jung; Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

6.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

7.  Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.

Authors:  Cole C Meyer; Zachary J Dubey; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-16       Impact factor: 15.336

8.  NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.

Authors:  Nicholas W Mszar; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-02-20       Impact factor: 15.419

9.  An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst.

Authors:  Hao Wu; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

10.  Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

Authors:  Charlotte A Osborne; Thomas B D Endean; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2015-10-27       Impact factor: 6.005
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