Literature DB >> 31550067

Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity.

Jan Sietmann1, Johannes M Wahl1.   

Abstract

Cyclobutanones hold a privileged role in enantioselective desymmetrization because their inherent ring strain allows for a variety of unusual reactions to occur. Current strategies include α-functionalization, rearrangement, and C-C bond activation to directly convert cyclobutanones into a wide range of enantiomerically enriched compounds, including many biologically significant scaffolds. This Minireview provides an overview of state-of-the-art methods that generate complexity from prochiral cyclobutanones in a single operation.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond activation; cyclobutanone; desymmetrization; quaternary stereocenters

Year:  2020        PMID: 31550067      PMCID: PMC7984208          DOI: 10.1002/anie.201910767

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   16.823


  64 in total

1.  Tracing the origins and evolution of chirality and handedness in chemical language.

Authors:  Pedro Cintas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Microbial Baeyer-Villiger oxidation: stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution.

Authors:  Marko D Mihovilovic; Florian Rudroff; Alexander Winninger; Toni Schneider; Frank Schulz; Manfred T Reetz
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005

3.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

4.  Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals.

Authors:  Laetitia Souillart; Nicolai Cramer
Journal:  Chem Rev       Date:  2015-06-05       Impact factor: 60.622

5.  α-Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones.

Authors:  Stanley Chang; Michael Holmes; Jeffrey Mowat; Michael Meanwell; Robert Britton
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-15       Impact factor: 15.336

6.  Intramolecular σ-bond metathesis between carbon-carbon and silicon-silicon bonds.

Authors:  Naoki Ishida; Wataru Ikemoto; Masahiro Murakami
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

7.  Palladium-catalyzed sequential carbon-carbon bond cleavage/formation producing arylated benzolactones.

Authors:  Takanori Matsuda; Masanori Shigeno; Masahiro Murakami
Journal:  Org Lett       Date:  2008-10-28       Impact factor: 6.005

8.  Pd-Catalyzed Enantioselective Ring Opening/Cross-Coupling and Cyclopropanation of Cyclobutanones.

Authors:  Jian Cao; Ling Chen; Feng-Na Sun; Yu-Li Sun; Ke-Zhi Jiang; Ke-Fang Yang; Zheng Xu; Li-Wen Xu
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-07       Impact factor: 15.336

9.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

10.  The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.

Authors:  Sean P Brown; Michael P Brochu; Christopher J Sinz; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

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  6 in total

1.  Organocatalytic enantioselective SN1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.

Authors:  Wen-Run Zhu; Qiong Su; Xiao-Yi Deng; Jia-Sheng Liu; Tao Zhong; Shan-Shui Meng; Ji-Tao Yi; Jiang Weng; Gui Lu
Journal:  Chem Sci       Date:  2021-11-23       Impact factor: 9.969

2.  Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction.

Authors:  Guan Zhang; Zhihan Zhang; Mengyuan Hou; Xinping Cai; Kai Yang; Peiyuan Yu; Qiuling Song
Journal:  Nat Commun       Date:  2022-05-12       Impact factor: 17.694

Review 3.  Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity.

Authors:  Jan Sietmann; Johannes M Wahl
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-19       Impact factor: 16.823

4.  Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols.

Authors:  Estefania Capel; Marta Rodríguez-Rodríguez; Uxue Uria; Manuel Pedron; Tomas Tejero; Jose L Vicario; Pedro Merino
Journal:  J Org Chem       Date:  2021-12-20       Impact factor: 4.354

5.  Nickel-Catalyzed Asymmetric Domino Ring Opening/Cross-Coupling Reaction of Cyclobutanones via a Reductive Strategy.

Authors:  Decai Ding; Haiyan Dong; Chuan Wang
Journal:  iScience       Date:  2020-04-03

6.  Puckering the Planar Landscape of Fragments: Design and Synthesis of a 3D Cyclobutane Fragment Library.

Authors:  David J Hamilton; Marieke Beemsterboer; Caroline M Carter; Jasmina Elsayed; Rilana E M Huiberts; Hanna F Klein; Peter O'Brien; Iwan J P de Esch; Maikel Wijtmans
Journal:  ChemMedChem       Date:  2022-03-30       Impact factor: 3.540

  6 in total

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