Literature DB >> 21639096

A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates.

Keith R Fandrick1, Daniel R Fandrick, Jonathan T Reeves, Joe Gao, Shengli Ma, Wenjie Li, Heewon Lee, Nelu Grinberg, Bruce Lu, Chris H Senanayake.   

Abstract

An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which γ-butyrolactones, β-hydroxy methyl ketones, and β-hydroxycarboxylates are readily obtained.

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Year:  2011        PMID: 21639096     DOI: 10.1021/ja2028958

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


  15 in total

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Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

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

8.  Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones.

Authors:  Yang Yang; Ian B Perry; Gang Lu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2016-06-09       Impact factor: 47.728

9.  Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.

Authors:  Barry M Trost; Dennis C Koester; Ehesan U Sharif
Journal:  Chemistry       Date:  2016-01-25       Impact factor: 5.236

10.  A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core.

Authors:  Nicholas G W Cowper; Matthew J Hesse; Katie M Chan; Sarah E Reisman
Journal:  Chem Sci       Date:  2020-10-15       Impact factor: 9.825

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