Literature DB >> 19473013

Allylation and crotylation of ketones and aldehydes using potassium organotrifluoroborate salts under Lewis acid and montmorillonite K10 catalyzed conditions.

Farhad Nowrouzi1, Avinash N Thadani, Robert A Batey.   

Abstract

Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF(3).OEt(2) and montmorillonite clay are used as catalysts to promote additions. The montmorillonite-catalyzed method in particular is very robust, providing a straightforward and scalable method for the allylation and crotylation of a range of ketones and aldehydes.

Entities:  

Year:  2009        PMID: 19473013     DOI: 10.1021/ol900599q

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

2.  Allyl transfer to aldehydes and ketones by Brønsted acid activation of allyl and crotyl 1,3,2-dioxazaborolidines.

Authors:  Maureen K Reilly; Scott D Rychnovsky
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

3.  Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

Authors:  Mihai Raducan; Rauful Alam; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

4.  Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.

Authors:  Kieran Nicholson; Yuxuan Peng; Natalia Llopis; Dominic R Willcox; Gary S Nichol; Thomas Langer; Alejandro Baeza; Stephen P Thomas
Journal:  ACS Catal       Date:  2022-08-22       Impact factor: 13.700

5.  Diastereodivergent combined carbometalation/zinc homologation/C-C fragmentation reaction as an efficient tool to prepare acyclic allylic quaternary carbon stereocenters.

Authors:  Sudipta Raha Roy; Dorian Didier; Amir Kleiner; Ilan Marek
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825

6.  Allylation of functionalized aldehydes by potassium allyltrifluoroborate catalyzed by 18-crown-6 in aqueous media.

Authors:  Fernanda C G Barbosa; Juliano C R Freitas; Caio F Melo; Paulo H Menezes; Roberta A Oliveira
Journal:  Molecules       Date:  2012-11-28       Impact factor: 4.411

  6 in total

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