Literature DB >> 23881865

The Mukaiyama aldol reaction: 40 years of continuous development.

Jun-ichi Matsuo1, Masahiro Murakami.   

Abstract

A directed cross-aldol reaction of silyl enol ethers with carbonyl compounds, such as aldehydes and ketones, promoted by a Lewis acid, a reaction which is now widely known as the Mukaiyama aldol reaction. It was first reported in 1973, and this year marks the 40th anniversary. The directed cross-aldol reactions mediated by boron enolates and tin(II) enolates also emerged from the Mukaiyama laboratory. These directed cross-aldol reactions have become invaluable tools for the construction of stereochemically complex molecules from two carbonyl compounds. This Minireview provides a succinct historical overview of their discoveries and the early stages of their development.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aldol reaction; history of science; silyl enol ether; stereoselectivity; synthetic methods

Mesh:

Substances:

Year:  2013        PMID: 23881865     DOI: 10.1002/anie.201303192

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


  28 in total

Review 1.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

Review 2.  Synthetic studies of viridiofungins, broad-spectrum antifungal agents and serine palmitoyl transferase inhibitors.

Authors:  Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Antibiot (Tokyo)       Date:  2017-09-27       Impact factor: 2.649

3.  Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure.

Authors:  Joan E Roque Peña; Erik J Alexanian
Journal:  Org Lett       Date:  2017-08-11       Impact factor: 6.005

4.  Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis.

Authors:  Steven M Banik; Anna Levina; Alan M Hyde; Eric N Jacobsen
Journal:  Science       Date:  2017-11-10       Impact factor: 47.728

5.  Investigation of Lewis Acid-Carbonyl Solution Interactions via Infrared-Monitored Titration.

Authors:  Carly S Hanson; Mary C Psaltakis; Janiel J Cortes; Sameera S Siddiqi; James J Devery
Journal:  J Org Chem       Date:  2019-12-27       Impact factor: 4.354

6.  Trapping the Complex Molecular Machinery of Polyketide and Fatty Acid Synthases with Tunable Silylcyanohydrin Crosslinkers.

Authors:  Sho Konno; James J La Clair; Michael D Burkart
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

7.  Combined Theoretical and Experimental Investigation of Lewis Acid-Carbonyl Interactions for Metathesis.

Authors:  Tanmay Malakar; Carly S Hanson; James J Devery; Paul M Zimmerman
Journal:  ACS Catal       Date:  2021-03-25       Impact factor: 13.084

8.  Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

Authors:  T E Anderson; Alexander A Andia; K A Woerpel
Journal:  Tetrahedron       Date:  2020-12-24       Impact factor: 2.457

9.  Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions.

Authors:  Natalie C Dwulet; Vincenzo Ramella; Christopher D Vanderwal
Journal:  Org Lett       Date:  2021-12-06       Impact factor: 6.005

10.  Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.

Authors:  Shengfei Jin; Hang T Dang; Graham C Haug; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2020-07-01       Impact factor: 9.825

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