Literature DB >> 27547839

A General Catalytic Asymmetric Prins Cyclization.

Luping Liu1, Philip S J Kaib1, Aurélien Tap1, Benjamin List1.   

Abstract

A new class of highly acidic confined imino-imidodiphosphate (iIDP) Brønsted acids catalyze the asymmetric Prins cyclization of both aliphatic and aromatic aldehydes. Diverse functionalized 4-methylenetetrahydropyrans are obtained in good to excellent yields and with good to excellent regio- and enantioselectivities. Our iIDP catalysts provide an efficient and scalable enantioselective approach to various fragrances, including rose oxide and doremox.

Entities:  

Year:  2016        PMID： 27547839     DOI： 10.1021/jacs.6b07240

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


  12 in total

1.  Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

Authors:  Dennis A Kutateladze; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 15.419

Review 2.  Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress.

Authors:  Zhigeng Lin; Baoying Huang; Lufeng Ouyang; Liyao Zheng
Journal:  Molecules       Date:  2022-06-02       Impact factor: 4.927

3.  Unveiling the Delicate Balance of Steric and Dispersion Interactions in Organocatalysis Using High-Level Computational Methods.

Authors:  Diana Yepes; Frank Neese; Benjamin List; Giovanni Bistoni
Journal:  J Am Chem Soc       Date:  2020-02-07       Impact factor: 15.419

4.  An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.

Authors:  Philipp Kramer; Jennifer Grimmer; Michael Bolte; Georg Manolikakes
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

5.  Disulfonimides versus Phosphoric Acids in Brønsted Acid Catalysis: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Reactivity.

Authors:  Kerstin Rothermel; Matej Žabka; Johnny Hioe; Ruth M Gschwind
Journal:  J Org Chem       Date:  2019-10-02       Impact factor: 4.354

6.  Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles.

Authors:  Pinglu Zhang; Nobuya Tsuji; Jie Ouyang; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-01-05       Impact factor: 15.419

7.  The Catalytic Asymmetric Intermolecular Prins Reaction.

Authors:  C David Díaz-Oviedo; Rajat Maji; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-11-30       Impact factor: 15.419

8.  Chiral Brønsted acid-catalyzed intramolecular SN2' reaction for enantioselective construction of a quaternary stereogenic center.

Authors:  Masahiro Shimizu; Jun Kikuchi; Azusa Kondoh; Masahiro Terada
Journal:  Chem Sci       Date:  2018-06-05       Impact factor: 9.825

9.  Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels-Alder Reactions of Cyclohexadienones with Cyclopentadiene.

Authors:  Santanu Ghosh; Sayantani Das; Chandra Kanta De; Diana Yepes; Frank Neese; Giovanni Bistoni; Markus Leutzsch; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

10.  Unified Approach to Imidodiphosphate-Type Brønsted Acids with Tunable Confinement and Acidity.

Authors:  Sebastian A Schwengers; Chandra Kanta De; Oleg Grossmann; Joyce A A Grimm; Natascha R Sadlowski; Gabriela G Gerosa; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 15.419
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