Literature DB >> 26834295

Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Kimberly S Petersen1.   

Abstract

The asymmetric desymmetrization of meso or prochiral compounds containing an all-carbon quaternary center is an attractive alternative to classical synthetic approaches aimed at the asymmetric formation of a new C-C bond. This review focuses on nonenzymatic desymmetrizations that utilize transition metal catalysts or organocatalysts to distinguish between enantiotopic groups to generate enantioenriched compounds containing all-carbon quaternary stereocenters.

Entities:  

Keywords:  all-carbon quatemary center; asymmetric; desymmetrization; organocatalysis; transition-metal catalysis

Year:  2015        PMID: 26834295      PMCID: PMC4730901          DOI: 10.1016/j.tetlet.2015.09.134

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  42 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Enantioselective suzuki reactions: catalytic asymmetric synthesis of compounds containing quaternary carbon centers.

Authors:  Michael C Willis; Luke H W Powell; Christelle K Claverie; Simon J Watson
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

Review 3.  Enantioselective enzymatic desymmetrizations in organic synthesis.

Authors:  Eduardo García-Urdiales; Ignacio Alfonso; Vicente Gotor
Journal:  Chem Rev       Date:  2005-01       Impact factor: 60.622

4.  Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals.

Authors:  Shan-Shui Meng; Yong Liang; Kou-Sen Cao; Lufeng Zou; Xing-Bang Lin; Hui Yang; K N Houk; Wen-Hua Zheng
Journal:  J Am Chem Soc       Date:  2014-08-25       Impact factor: 15.419

5.  Enantioselective C-C bond cleavage creating chiral quaternary carbon centers.

Authors:  Takanori Matsuda; Masanori Shigeno; Masaomi Makino; Masahiro Murakami
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

6.  Asymmetric copper(I)-catalyzed azide-alkyne cycloaddition to quaternary oxindoles.

Authors:  Feng Zhou; Chen Tan; Jing Tang; Yan-Yan Zhang; Wei-Ming Gao; Hai-Hong Wu; Yi-Hua Yu; Jian Zhou
Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419

7.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

8.  Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

Authors:  Gregory C Fu
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.

Authors:  Qin Liu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

10.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

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  7 in total

1.  Biomimetic Desymmetrization of a Carboxylic Acid.

Authors:  Matthew T Knowe; Michael W Danneman; Sarah Sun; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-02-05       Impact factor: 15.419

2.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

3.  Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers.

Authors:  Jung-Woo Park; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419

4.  Distal Ionic Substrate-Catalyst Interactions Enable Long-Range Stereocontrol: Access to Remote Quaternary Stereocenters through a Desymmetrizing Suzuki-Miyaura Reaction.

Authors:  Yazhou Lou; Junqiang Wei; Mingfeng Li; Ye Zhu
Journal:  J Am Chem Soc       Date:  2022-01-03       Impact factor: 16.383

5.  Auto-Tandem Catalysis: PdII -Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones.

Authors:  Claire J C Lamb; Bryan G Nderitu; Gemma McMurdo; John M Tobin; Filipe Vilela; Ai-Lan Lee
Journal:  Chemistry       Date:  2017-11-30       Impact factor: 5.236

6.  Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.

Authors:  Jie Luo; Qingxiang Cao; Xiaohui Cao; Xiaodan Zhao
Journal:  Nat Commun       Date:  2018-02-06       Impact factor: 14.919

7.  Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination.

Authors:  Zhang-Long Yu; Yong-Feng Cheng; Na-Chuan Jiang; Jian Wang; Li-Wen Fan; Yue Yuan; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Chem Sci       Date:  2020-05-20       Impact factor: 9.825

  7 in total

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