Literature DB >> 25411552

Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Yi Luan1, Yue Qi2, Hongyi Gao1, Qianqian Ma1, Scott E Schaus2.   

Abstract

A novel Brønsted acid/Lewis acid dual catalyst system has been developed to promote an efficient C-C bond formation between a range of oxocarbenium precursors derived from chromene acetals and ethyl diazoacetate. The reaction proceeds under mild conditions and is tolerant of common functionalized 2H-chromene and isochromene acetals. In addition, an asymmetric variant of diazoacetate addition towards 2H-chromene acetal is described. Continued investigations include the further optimization of asymmetric induction towards the formation of diazo ester substituted 2H-chromene.

Entities:  

Keywords:  Brønsted Acid; Diazo compounds; Enantioselectivity; Lewis acid; Oxocarbenium

Year:  2014        PMID： 25411552      PMCID： PMC4233145          DOI： 10.1002/ejoc.201403043

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  26 in total

1.  Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

Authors:  Wengang Yao; Jianbo Wang
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

2.  Titanium(IV)-catalyzed dynamic kinetic asymmetric transformation of alcohols, silyl ethers, and acetals under carbon allylation.

Authors:  Manfred Braun; Wolfgang Kotter
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-16       Impact factor: 15.336

3.  Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.

Authors:  Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

4.  Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

Authors:  Noah Z Burns; Michael R Witten; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-08-25       Impact factor: 15.419

5.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Authors:  Pankaj Jain; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

6.  Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors:  Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

7.  Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization.

Authors:  Lydia J Rono; Hatice G Yayla; David Y Wang; Michael F Armstrong; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2013-11-13       Impact factor: 15.419

8.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors:  Daisuke Uraguchi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

9.  Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

Authors:  Magnus Rueping; Chandra M R Volla; Iuliana Atodiresei
Journal:  Org Lett       Date:  2012-08-22       Impact factor: 6.005

10.  Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

Authors:  Barry M Trost; Sushant Malhotra; Benjamin A Fried
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419
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