Literature DB >> 25784558

Ortho-quinone methides as reactive intermediates in asymmetric brønsted Acid catalyzed cycloadditions with unactivated alkenes by exclusive activation of the electrophile.

Chien-Chi Hsiao1, Sadiya Raja, Hsuan-Hung Liao, Iuliana Atodiresei, Magnus Rueping.   

Abstract

An efficient method for the highly enantioselective synthesis of chiral chromanes bearing multiple stereogenic centers was developed. A chiral BINOL-based N-triflylphosphoramide proved to be an effective catalyst for the in situ generation of ortho-quinone methides (o-QMs) and their subsequent cycloaddition reaction with unactivated alkenes provided chromanes with excellent diastereo- and enantioselectivity.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chromanes; cycloaddition; homogeneous catalysis; n-triflylphosphoramide; ortho-quinone methide

Year:  2015        PMID： 25784558     DOI： 10.1002/anie.201409850

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


  14 in total

1.  Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Authors:  Zhenyu Yang; Ying He; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-07-29       Impact factor: 15.419

2.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

3.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

4.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

5.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

6.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

7.  Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

Authors:  Carlos Jarava-Barrera; Alejandro Parra; Aurora López; Fabio Cruz-Acosta; Daniel Collado-Sanz; Diego J Cárdenas; Mariola Tortosa
Journal:  ACS Catal       Date:  2015-12-11       Impact factor: 13.084

8.  Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

Authors:  Katharina Zielke; Mario Waser
Journal:  Org Lett       Date:  2018-01-19       Impact factor: 6.005

9.  Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins' vs. 'ortho-quinone methide cycloaddition' mechanistic nexus.

Authors:  Christian D-T Nielsen; Wouter J Mooij; David Sale; Henry S Rzepa; Jordi Burés; Alan C Spivey
Journal:  Chem Sci       Date:  2018-10-19       Impact factor: 9.825

10.  Cooperative Catalysis for the Highly Diastereo- and Enantioselective [4+3]-Cycloannulation of ortho-Quinone Methides and Carbonyl Ylides.

Authors:  Arun Suneja; Henning Jakob Loui; Christoph Schneider
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-23       Impact factor: 15.336
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