Literature DB >> 21226456

Enantioselective [3 + 2] cycloaddition of allenes to acrylates catalyzed by dipeptide-derived phosphines: facile creation of functionalized cyclopentenes containing quaternary stereogenic centers.

Xiaoyu Han1, Youqing Wang, Fangrui Zhong, Yixin Lu.   

Abstract

A new family of dipeptide-based chiral phosphines was designed and prepared. D-Thr-L-tert-Leu-derived catalyst 4c promoted [3 + 2] cycloaddition of allenoates to α-substituted acrylates in a regiospecific and stereoselective manner, furnishing functionalized cyclopentenes with quaternary stereogenic centers in high yields and with excellent enantioselectivities.

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Year:  2011        PMID: 21226456     DOI: 10.1021/ja1106282

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  26 in total

1.  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 2.  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

3.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

4.  Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters.

Authors:  Yuji Fujiwara; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

5.  Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.

Authors:  Chengfeng Jing; Risong Na; Bo Wang; Honglei Liu; Lei Zhang; Jun Liu; Min Wang; Jiangchun Zhong; Ohyun Kwon; Hongchao Guo
Journal:  Adv Synth Catal       Date:  2012-04-26       Impact factor: 5.837

6.  Scope and mechanistic investigations of Pd-catalyzed coupling/cyclizations and cycloisomerizations of allenyl malonates.

Authors:  Logan E Vine; Ryan D Reeves; Eleanor M Landwehr; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2021-07-15       Impact factor: 13.700

7.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

8.  Biphenyl-derived phosphepines as chiral nucleophilic catalysts: enantioselective [4+1] annulations to form functionalized cyclopentenes.

Authors:  Daniel T Ziegler; Lorena Riesgo; Takuya Ikeda; Yuji Fujiwara; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-06       Impact factor: 15.336

9.  Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction.

Authors:  Marianne Steurer; Kim L Jensen; Dennis Worgull; Karl Anker Jørgensen
Journal:  Chemistry       Date:  2011-12-07       Impact factor: 5.236

10.  Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates with maleimides.

Authors:  Hong-Ping Deng; De Wang; Yin Wei; Min Shi
Journal:  Beilstein J Org Chem       Date:  2012-07-16       Impact factor: 2.883

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