Literature DB >> 29400455

Biomimetic Desymmetrization of a Carboxylic Acid.

Matthew T Knowe1, Michael W Danneman1, Sarah Sun1, Maren Pink2, Jeffrey N Johnston1.   

Abstract

The enantioselective desymmetrization of carboxylic acids by chiral Brønsted base catalysis is reported, leading to bridged bicyclic lactones with up to 94% ee. Crystallographic analysis of a substrate-catalyst complex suggests an origin of stereocontrol, reminiscent of functional Brønsted bases in biological settings, and enabled reaction optimization. The products contain an all-carbon quaternary stereocenter and can be derivatized to functionalized cyclopentanes.

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Year:  2018        PMID： 29400455      PMCID： PMC5814305          DOI： 10.1021/jacs.7b12185

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


  47 in total

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Authors:  Jürgen Haas; Sandrine Piguel; Thomas Wirth
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

Review 2.  New catalytic approaches towards the enantioselective halogenation of alkenes.

Authors:  Ulrich Hennecke
Journal:  Chem Asian J       Date:  2012-02-07

3.  Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: enantioselective arylation of enecarbamates.

Authors:  Takuya Hashimoto; Hiroki Nakatsu; Yuka Takiguchi; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2013-10-22       Impact factor: 15.419

Review 4.  Asymmetric Brønsted acid catalysis with chiral carboxylic acids.

Authors:  Chang Min; Daniel Seidel
Journal:  Chem Soc Rev       Date:  2017-10-02       Impact factor: 54.564

5.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

6.  C3-symmetric trisimidazoline-catalyzed enantioselective bromolactonization of internal alkenoic acids.

Authors:  Kenichi Murai; Akira Nakamura; Tomoyo Matsushita; Masato Shimura; Hiromichi Fujioka
Journal:  Chemistry       Date:  2012-05-23       Impact factor: 5.236

Review 7.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

8.  Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

Authors:  Akira Sakakura; Atsushi Ukai; Kazuaki Ishihara
Journal:  Nature       Date:  2007-02-22       Impact factor: 49.962

9.  DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

Authors:  Wen Zhang; Huadong Xu; Hui Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

10.  Brønsted acid catalyzed phosphoramidic acid additions to alkenes: diastereo- and enantioselective halogenative cyclizations for the synthesis of C- and P-chiral phosphoramidates.

Authors:  Yasunori Toda; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2014-10-14       Impact factor: 15.419
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  4 in total

1.  Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO2-Capture: Discovery, Development, and Mechanism.

Authors:  Roozbeh Yousefi; Thomas J Struble; Jenna L Payne; Mahesh Vishe; Nathan D Schley; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-12-24       Impact factor: 15.419

2.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354

3.  Association of Halogen Bonding and Hydrogen Bonding in Metal Acetate-Catalyzed Asymmetric Halolactonization.

Authors:  Takayoshi Arai; Kodai Horigane; Ohji Watanabe; Junki Kakino; Noriyuki Sugiyama; Hiroki Makino; Yuto Kamei; Shinnosuke Yabe; Masahiro Yamanaka
Journal:  iScience       Date:  2019-01-23

4.  Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.

Authors:  Jenna L Payne; Zihang Deng; Andrew L Flach; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2022-06-08       Impact factor: 9.969
  4 in total

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