Literature DB >> 19212998

Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.

Ying Kit Chung1, Gregory C Fu.   

Abstract

Chiral phosphepine 1 catalyzes the transformation of an array of hydroxy-2-alkynoates into saturated oxygen heterocycles with good enantioselectivity. Phenols are also shown to participate in such phosphine-catalyzed cyclizations, including an asymmetric variant. This method provides a new approach to the enantioselective synthesis of tetrahydrofurans, tetrahydropyrans, and dihydrobenzopyrans.

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Year:  2009        PMID： 19212998      PMCID： PMC2747790          DOI： 10.1002/anie.200805377

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

1.  Enantioselective Acylations Catalyzed by Chiral Phosphines.

Authors:  E. Vedejs; O. Daugulis; S. T. Diver
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

2.  Enantioselective hydrogenation of beta-ketoesters with monodentate ligands.

Authors:  Kathrin Junge; Bernhard Hagemann; Stephan Enthaler; Günther Oehme; Manfred Michalik; Axel Monsees; Thomas Riermeier; Uwe Dingerdissen; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2004-09-27       Impact factor: 15.336

3.  Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes.

Authors:  Ryan P Wurz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-09-07       Impact factor: 15.419

4.  Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing alpha-amino acid.

Authors:  Bryan J Cowen; Scott J Miller
Journal:  J Am Chem Soc       Date:  2007-08-21       Impact factor: 15.419

5.  Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins.

Authors:  Min Shi; Lian-Hui Chen; Chao-Qun Li
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

6.  Synthesis and application of chiral spiro phospholane ligand in Pd-catalyzed asymmetric allylation of aldehydes with allylic alcohols.

Authors:  Shou-Fei Zhu; Yun Yang; Li-Xin Wang; Bin Liu; Qi-Lin Zhou
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

Review 7.  Phosphine-triggered synthesis of functionalized cyclic compounds.

Authors:  Long-Wu Ye; Jian Zhou; Yong Tang
Journal:  Chem Soc Rev       Date:  2008-03-26       Impact factor: 54.564

8.  2-Phospha[3]ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations.

Authors:  Arnaud Voituriez; Armen Panossian; Nicolas Fleury-Brégeot; Pascal Retailleau; Angela Marinetti
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

9.  Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions.

Authors:  Jian-Hua Xie; Qi-Lin Zhou
Journal:  Acc Chem Res       Date:  2008-03-01       Impact factor: 22.384

10.  Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions.

Authors:  Yuan-Qing Fang; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-04-08       Impact factor: 15.419
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  34 in total

1.  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

2.  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

3.  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

4.  Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones.

Authors:  Antoinette E Nibbs; Karl A Scheidt
Journal:  European J Org Chem       Date:  2011-12-09

5.  Phosphine-Mediated Iterative Arene Homologation Using Allenes.

Authors:  Kui Zhang; Lingchao Cai; Xing Jiang; Miguel A Garcia-Garibay; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

Review 6.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

7.  Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

Authors:  Anastassia Matviitsuk; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

8.  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

9.  Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

Authors:  Barry M Trost; Alicia C Gutierrez; Robert C Livingston
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

10.  Stereoselective phosphine-catalyzed synthesis of highly functionalized diquinanes.

Authors:  Jonathan E Wilson; Jianwei Sun; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336
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