Literature DB >> 27122466

Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl.

Wen Yang1, Zhaobin Wang1, Jianwei Sun2.   

Abstract

An unprecedented enantioselective oxetane opening with chloride provides access to a range of highly functionalized three-carbon building blocks. The excellent enantiocontrol is enabled not only by a new catalyst, but also by the unusual use of wet molecular sieves for the controlled release of HCl.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; desymmetrization; organocatalysis; oxetanes; strained molecules

Year:  2016        PMID： 27122466     DOI： 10.1002/anie.201601844

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.  Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.

Authors:  Ransheng Ding; Christian Wolf
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

3.  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

4.  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

5.  Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.

Authors:  Mingxu Li; Jian Zhang; Yashi Zou; Fengfan Zhou; Zhenfeng Zhang; Wanbin Zhang
Journal:  Chem Sci       Date:  2021-10-28       Impact factor: 9.825

6.  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

7.  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

8.  A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

Authors:  Daniel A Strassfeld; Russell F Algera; Zachary K Wickens; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

9.  Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves.

Authors:  Weiwei Luo; Zhicheng Sun; E H Nisala Fernando; Vladimir N Nesterov; Thomas R Cundari; Hong Wang
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825

10.  Bioinspired Cobalt-Catalysis Enables Generation of Nucleophilic Radicals from Oxetanes.

Authors:  Aleksandra Potrząsaj; Michał Ociepa; Wojciech Chaładaj; Dorota Gryko
Journal:  Org Lett       Date:  2022-03-25       Impact factor: 6.005
  10 in total

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