Literature DB >> 18433122

One-pot multi-component asymmetric cascade reactions catalyzed by soluble star polymers with highly branched non-interpenetrating catalytic cores.

Yonggui Chi1, Steven T Scroggins, Jean M J Fréchet.   

Abstract

Non-interpenetrating star polymer catalysts designed to mimic the site isolation characteristics of enzymes enable the one-pot combination of multiple otherwise incompatible catalysts for asymmetric cascade reactions that involve iminium, enamine, and H-bonding catalysis. Control experiments replacing star polymer catalysts with the corresponding small molecule or linear polymer analogues lead to little or no cascade reaction. Our strategy also allows straightforward access to all possible stereoisomers of the cascade product individually by proper choice of catalyst chirality. To our knowledge, this work represents the most sophisticated study of soluble polymers for site isolation, enzyme-like catalysis that generates cascade products with multiple chiral centers.

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Year:  2008        PMID: 18433122     DOI: 10.1021/ja8013456

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

1.  Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors:  Kerem E Ozboya; Tomislav Rovis
Journal:  Chem Sci       Date:  2011-09-01       Impact factor: 9.825

2.  Nanogel star polymer architectures: a nanoparticle platform for modular programmable macromolecular self-assembly, intercellular transport, and dual-mode cargo delivery.

Authors:  Victor Y Lee; Karen Havenstrite; Melia Tjio; Melanie McNeil; Helen M Blau; Robert D Miller; Joseph Sly
Journal:  Adv Mater       Date:  2011-09-08       Impact factor: 30.849

3.  Environmental Modulation of Chiral Prolinamide Catalysts for Stereodivergent Conjugate Addition.

Authors:  Xiaowei Li; Yan Zhao
Journal:  J Catal       Date:  2022-01-10       Impact factor: 7.920

4.  Cycle-specific organocascade catalysis: application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis.

Authors:  Bryon Simmons; Abbas M Walji; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Asymmetric one-pot sequential Friedel-Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme.

Authors:  Kengo Akagawa; Ryota Umezawa; Kazuaki Kudo
Journal:  Beilstein J Org Chem       Date:  2012-08-17       Impact factor: 2.883

6.  Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel-Crafts reactions with a chiral bifunctional heterogeneous catalyst.

Authors:  Hong-Gang Cheng; Javier Miguélez; Hiroyuki Miyamura; Woo-Jin Yoo; Shū Kobayashi
Journal:  Chem Sci       Date:  2016-10-05       Impact factor: 9.825

7.  A multifunctional surfactant catalyst inspired by hydrolases.

Authors:  Mitchell D Nothling; Zeyun Xiao; Nicholas S Hill; Mitchell T Blyth; Ayana Bhaskaran; Marc-Antoine Sani; Andrea Espinosa-Gomez; Kevin Ngov; Jonathan White; Tim Buscher; Frances Separovic; Megan L O'Mara; Michelle L Coote; Luke A Connal
Journal:  Sci Adv       Date:  2020-04-01       Impact factor: 14.136

8.  Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with ketones.

Authors:  Gonglin Li; Yan Zhang; Hongkun Zeng; Xiaoming Feng; Zhishan Su; Lili Lin
Journal:  Chem Sci       Date:  2022-03-22       Impact factor: 9.825

9.  Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality.

Authors:  Jose I Martínez; Uxue Uria; Maria Muñiz; Efraím Reyes; Luisa Carrillo; Jose L Vicario
Journal:  Beilstein J Org Chem       Date:  2015-12-14       Impact factor: 2.883

10.  Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans.

Authors:  Charlie Verrier; Paolo Melchiorre
Journal:  Chem Sci       Date:  2015-04-27       Impact factor: 9.825

  10 in total

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