Literature DB >> 22419060

Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines.

Hua Xiao1, Zhuo Chai, Dongdong Cao, Hongyu Wang, Jinghao Chen, Gang Zhao.   

Abstract

An asymmetric organocatalytic [4 + 2] cycloaddition between α-substituted allenoates and dual activated olefins using bifunctional N-acyl aminophosphine catalysts is described. The use of 2-cyano acrylate derived olefins led to the first successful incorporation of an electrophile derived from an aliphatic aldehyde into this reaction. This journal is © The Royal Society of Chemistry 2012

Entities:  

Year:  2012        PMID: 22419060     DOI: 10.1039/c2ob25295c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  11 in total

Review 1.  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

2.  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

3.  Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.

Authors:  Nathan J Dupper; Ohyun Kwon
Journal:  Org Lett       Date:  2015-02-11       Impact factor: 6.005

4.  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

Review 5.  Phosphine catalysis of allenes with electrophiles.

Authors:  Zhiming Wang; Xingzhu Xu; Ohyun Kwon
Journal:  Chem Soc Rev       Date:  2014-03-24       Impact factor: 54.564

6.  Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.

Authors:  Andreas Eitzinger; Katharina Zielke; Michael Widhalm; Raphaël Robiette; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-05-04       Impact factor: 3.319

Review 7.  Organophosphine-Catalyzed [4C+X] Annulations.

Authors:  Yangyan Li; Xiang Chen; Xiaoming Chen; Xiao Shen
Journal:  Molecules       Date:  2018-11-19       Impact factor: 4.411

Review 8.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

9.  Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts.

Authors:  Qiao-Wen Jin; Zhuo Chai; You-Ming Huang; Gang Zou; Gang Zhao
Journal:  Beilstein J Org Chem       Date:  2016-04-15       Impact factor: 2.883

10.  Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.

Authors:  Weijun Yao; Zhaoyuan Yu; Shan Wen; Huanzhen Ni; Nisar Ullah; Yu Lan; Yixin Lu
Journal:  Chem Sci       Date:  2017-05-17       Impact factor: 9.825

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