Literature DB >> 19847345

Enantioselective catalysis and complexity generation from allenoates.

Bryan J Cowen1, Scott J Miller.   

Abstract

Lewis base catalysis of reactions with allenoates using phosphine and amine nucleophiles has emerged as a key platform for the generation of molecular complexity. Investigations in this area have established a range of suitable coupling partners for allenoates, including electron-deficient olefins, imines, and aldehydes. This tutorial review will describe these methodologies, with a special emphasis on recent work regarding asymmetric reactions using chiral Lewis base catalysts.

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Year:  2009        PMID: 19847345     DOI: 10.1039/b816700c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  49 in total

1.  Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.

Authors:  Judy Szeto; Vardhineedi Sriramurthy; Ohyun Kwon
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

2.  Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

3.  Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Org Lett       Date:  2015-04-14       Impact factor: 6.005

4.  Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.

Authors:  Tioga J Martin; Venus G Vakhshori; Yang S Tran; Ohyun Kwon
Journal:  Org Lett       Date:  2011-04-14       Impact factor: 6.005

5.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

6.  Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.

Authors:  Qing-Fa Zhou; Kui Zhang; Ohyun Kwon
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

7.  Equilibrium between a vinylogous ylide and a phosphonium dienolate zwitterion: vinylogous Wittig olefination versus vinylogous aldol-type reaction.

Authors:  San N Khong; Yang S Tran; Ohyun Kwon
Journal:  Tetrahedron       Date:  2010-06       Impact factor: 2.457

8.  Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

Authors:  Riccardo Sinisi; Jianwei Sun; Gregory C Fu
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-12       Impact factor: 11.205

9.  Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.

Authors:  Yang S Tran; Tioga J Martin; Ohyun Kwon
Journal:  Chem Asian J       Date:  2011-07-07

10.  PHOSPHINE-CATALYZED [3 + 2] ANNULATION: SYNTHESIS OF ETHYL 5-(tert-BUTYL)-2-PHENYL-1-TOSYL-3-PYRROLINE-3-CARBOXYLATE.

Authors:  Ian P Andrews; Ohyun Kwon
Journal:  Organic Synth       Date:  2012
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