Literature DB >> 22851505

Asymmetric Brønsted acid-catalyzed nazarov cyclization of acyclic α-alkoxy dienones.

Sadiya Raja1, Winai Ieawsuwan, Vadim Korotkov, Magnus Rueping.   

Abstract

A Brønsted acid-catalyzed asymmetric Nazarov cyclization of acyclic α-alkoxy dienones has been developed. The reaction offers access to chiral cyclopentenones in a highly enantioselective manner. The reaction is complementary to our previously reported Brønsted acid-catalyzed electrocyclization reactions, which provided differently substituted optically active cyclopentenones with a fused tetrahydropyrane ring in good yields and with excellent enantioselectivities.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22851505     DOI: 10.1002/asia.201200391

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  5 in total

1.  Enyne diketones as substrate in asymmetric Nazarov cyclization for construction of chiral allene cyclopentenones.

Authors:  Shengbiao Tang; Peng Zhang; Ying Shao; Jiangtao Sun
Journal:  Nat Commun       Date:  2022-06-07       Impact factor: 17.694

2.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005

3.  Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones.

Authors:  Jie Ouyang; Jennifer L Kennemur; Chandra Kanta De; Christophe Farès; Benjamin List
Journal:  J Am Chem Soc       Date:  2019-02-15       Impact factor: 15.419

4.  Asymmetric Gold(I)-Catalyzed Tandem Hydroarylation-Nazarov Cyclization: Enantioselective Access to Cyclopentenones.

Authors:  Marta Solas; Samuel Suárez-Pantiga; Roberto Sanz
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-18       Impact factor: 16.823

5.  Salen promoted enantioselective Nazarov cyclizations of activated and unactivated dienones.

Authors:  Gerri E Hutson; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-03-25       Impact factor: 15.419

  5 in total

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