Literature DB >> 18497927

Phosphine-triggered synthesis of functionalized cyclic compounds.

Long-Wu Ye1, Jian Zhou, Yong Tang.   

Abstract

Nucleophilic phosphine catalysis has proven to be a powerful tool in organic synthesis, which can provide easy access to cyclic, bicyclic or polycyclic carbocycles and heterocycles. Owing to their comparatively strong and readily tunable nucleophilicity, phosphines can be easily tailored to efficient annulation reactions with good control over reaction selectivity. This has resulted in a tremendous increase in their scope and in a concomitant number of reports where phosphine-triggered annulation reactions occur. This tutorial review summarizes the recent achievements in this area.

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Year:  2008        PMID: 18497927     DOI: 10.1039/b717758e

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


  51 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 [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

9.  Asymmetric carbon-carbon bond formation gamma to a carbonyl group: phosphine-catalyzed addition of nitromethane to allenes.

Authors:  Sean W Smith; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

10.  Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.

Authors:  Ying Kit Chung; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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