Literature DB >> 17039558

Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives.

Henrik Sundén1, Ismail Ibrahem, Gui-Ling Zhao, Lars Eriksson, Armando Córdova.   

Abstract

The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and alpha,beta-unsaturated aldehydes proceed with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%.

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Year:  2007        PMID： 17039558     DOI： 10.1002/chem.200600572

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  9 in total

1.  Synthesis of Deuterated Benzopyran Derivatives as Selective COX-2 Inhibitors with Improved Pharmacokinetic Properties.

Authors:  Yanmei Zhang; Micky D Tortorella; Yican Wang; Jianqi Liu; Zhengchao Tu; Xiaorong Liu; Yang Bai; Dingsheng Wen; Xin Lu; Yongzhi Lu; John J Talley
Journal:  ACS Med Chem Lett       Date:  2014-07-27       Impact factor: 4.345

2.  An organocascade kinetic resolution.

Authors:  Patrick G McGarraugh; Stacey E Brenner-Moyer
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

3.  Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.

Authors:  Harshkumar H Patel; Matthew B Prater; Scott O Squire; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-04-27       Impact factor: 15.419

4.  Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

Authors:  Bhaskar C Das; Seetaram Mohapatra; Philip D Campbell; Sabita Nayak; Sakkarapalayam M Mahalingam; Todd Evans
Journal:  Tetrahedron Lett       Date:  2010-05-01       Impact factor: 2.415

5.  Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.

Authors:  Nilanjana Majumdar; Keith A Korthals; William D Wulff
Journal:  J Am Chem Soc       Date:  2011-12-16       Impact factor: 15.419

6.  Catalytic enantioselective alpha-acylvinyl anion reactions of silyloxyallenes.

Authors:  Troy E Reynolds; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

8.  An optically active isochroman-2H-chromene conjugate potently suppresses neuronal oxidative injuries associated with the PI3K/Akt and MAPK signaling pathways.

Authors:  Ling-Xue Tao; Sha-Sha Ji; Dóra Szalóki; Tibor Kovács; Attila Mándi; Sándor Antus; Xun Ding; Tibor Kurtán; Hai-Yan Zhang
Journal:  Acta Pharmacol Sin       Date:  2020-05-11       Impact factor: 6.150

9.  Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines.

Authors:  Chittaranjan Bhanja; Satyaban Jena; Sabita Nayak; Seetaram Mohapatra
Journal:  Beilstein J Org Chem       Date:  2012-10-04       Impact factor: 2.883
  9 in total

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