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Literature DB >> 22852800

Organocatalytic one-pot asymmetric synthesis of 4H,5H-pyrano[2,3-c]pyrazoles.

Dieter Enders¹, André Grossmann, Bianca Gieraths, Muharrem Düzdemir, Carina Merkens.

Abstract

An efficient one pot asymmetric synthesis of tetrahydropyrano[2,3-c]pyrazoles has been developed. This class of biologically active heterocycles can be obtained via a secondary amine catalyzed asymmetric Michael/Wittig/oxa-Michael reaction sequence. Remarkably, the title compounds were accessible in good to very good yields and very good to excellent enantioselectivities after a single purification step.

Entities: Chemical

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Year: 2012 PMID： 22852800 DOI： 10.1021/ol301983f

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

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Cited

7 in total

1. Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3-c] pyrazoles under ultrasound irradiation.

Authors: Keyume Ablajan; Wang Liju; Yakefujiang Kelimu; Feng Jun
Journal: Mol Divers Date: 2013-08-06 Impact factor: 2.943

2. TFA-mediated synthesis of functionalized pyrano[2,3-c]pyrazoles from pyrazol-3-ones, active carbonyl compounds and tert-BuOH.

Authors: Issa Yavari; Jamil Sheykhahmadi
Journal: Mol Divers Date: 2021-03-02 Impact factor: 2.943

3. Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles.

Authors: Daniel Hack; Pankaj Chauhan; Kristina Deckers; Yusuke Mizutani; Gerhard Raabe; Dieter Enders
Journal: Chem Commun (Camb) Date: 2015-02-11 Impact factor: 6.222

4. 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

Organocatalytic one-pot asymmetric synthesis of 4H,5H-pyrano[2,3-c]pyrazoles.

1. Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3-c] pyrazoles under ultrasound irradiation.

2. TFA-mediated synthesis of functionalized pyrano[2,3-c]pyrazoles from pyrazol-3-ones, active carbonyl compounds and tert-BuOH.

3. Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles.

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

Review 5. Recent Advances in Organocatalyzed Domino C-C Bond-Forming Reactions.

6. Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds.

7. Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions.