Literature DB >> 26015083

The organocatalytic asymmetric Prins cyclization.

Gavin Chit Tsui1, Luping Liu1, Benjamin List2.   

Abstract

We describe here the design and development of an organocatalytic Prins cyclization. In the presence of a confined chiral imidodiphosphoric acid catalyst, salicylaldehydes react with 3-methyl-3-buten-1-ol to afford highly functionalized 4-methylenetetrahydropyrans in excellent regio- and enantioselectivity. The extreme steric demand of the acid catalyst is key for the success of this transformation.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; Prins cyclization; asymmetric catalysis; organocatalysis; tetrahydropyrans

Year:  2015        PMID： 26015083     DOI： 10.1002/anie.201500219

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


  9 in total

1.  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

2.  Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives.

Authors:  Gang Wang; Xiaodong Xin; Zehua Wang; Gang Lu; Yudao Ma; Lei Liu
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

3.  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

4.  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

5.  Copper-catalysed enantioselective intramolecular etherification of propargylic esters: synthetic approach to chiral isochromans.

Authors:  Shiyao Liu; Kazunari Nakajima; Yoshiaki Nishibayashi
Journal:  RSC Adv       Date:  2019-06-17       Impact factor: 3.361

6.  Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums.

Authors:  Xingxing Wu; Christof Sparr
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-25       Impact factor: 16.823

Review 7.  Recent Advances in the Prins Reaction.

Authors:  Efraim Reyes; Liher Prieto; Uxue Uria; Luisa Carrillo; Jose L Vicario
Journal:  ACS Omega       Date:  2022-08-31

8.  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

9.  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
  9 in total

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