Literature DB >> 26689744

Organocatalytic Enantioselective Synthesis of 1,4-Dioxanes and Other Oxa-Heterocycles by Oxetane Desymmetrization.

Wen Yang1, Jianwei Sun2.   

Abstract

A new asymmetric synthesis of chiral 1,4-dioxanes and other oxa-heterocycles has been developed by means of organocatalytic enantioselective desymmetrization of oxetanes. This mild process proceeds with exceedingly high efficiency and enantioselectivity to establish the quaternary stereocenters. This method complements the existing, yet limited, strategies for the synthesis of these oxa-heterocycles.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; cyclizations; heterocycles; hydrogen bonds; organocatalysis

Year:  2015        PMID： 26689744     DOI： 10.1002/anie.201509888

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


  10 in total

1.  Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes.

Authors:  Daniel A Strassfeld; Zachary K Wickens; Elias Picazo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-05-06       Impact factor: 15.419

2.  Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.

Authors:  Juan J Rojas; Elena Torrisi; Maryne A J Dubois; Riashat Hossain; Andrew J P White; Giovanni Zappia; James J Mousseau; Chulho Choi; James A Bull
Journal:  Org Lett       Date:  2022-03-21       Impact factor: 6.005

3.  Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.

Authors:  Alexander Sandvoß; Henning Maag; Constantin G Daniliuc; Dieter Schollmeyer; Johannes M Wahl
Journal:  Chem Sci       Date:  2022-05-04       Impact factor: 9.969

4.  Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Authors:  Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal:  Chem Sci       Date:  2017-01-23       Impact factor: 9.825

5.  Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres.

Authors:  Rosemary A Croft; James J Mousseau; Chulho Choi; James A Bull
Journal:  Chemistry       Date:  2017-12-20       Impact factor: 5.236

6.  Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles.

Authors:  Chen-Yan Cai; Hai-Chao Xu
Journal:  Nat Commun       Date:  2018-09-03       Impact factor: 14.919

7.  A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products.

Authors:  Hai Huang; Wen Yang; Zuliang Chen; Zengwei Lai; Jianwei Sun
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825

8.  Identifying the true origins of selectivity in chiral phosphoric acid catalyzed N-acyl-azetidine desymmetrizations.

Authors:  Pier Alexandre Champagne
Journal:  Chem Sci       Date:  2021-11-23       Impact factor: 9.825

9.  Unexpected Isomerization of Oxetane-Carboxylic Acids.

Authors:  Bohdan Chalyk; Anastasiia Grynyova; Kateryna Filimonova; Tymofii V Rudenko; Dmitry Dibchak; Pavel K Mykhailiuk
Journal:  Org Lett       Date:  2022-06-29       Impact factor: 6.072

10.  3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions.

Authors:  Zengwei Lai; Renwei Zhang; Qiang Feng; Jianwei Sun
Journal:  Chem Sci       Date:  2020-09-08       Impact factor: 9.825
  10 in total

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