Literature DB >> 26041942

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

Qing-Fa Zhou1, Kui Zhang1, Ohyun Kwon1.   

Abstract

α,β-Unsaturated γ-amino esters can be synthesized efficiently and stereoselectively through phosphine-catalyzed γ-umpolung additions of sulfonamides to γ-substituted allenoates. The structures of the sulfonamide and γ-substituted allenoate partners can be varied to achieve a range of α,β-unsaturated γ-amino esters with potentially interesting chemical and biological properties.

Entities:  

Keywords:  phosphine; stereoselective synthesis; γ-substituted allenoate; γ-umpolung addition

Year:  2015        PMID: 26041942      PMCID: PMC4450090          DOI: 10.1016/j.tetlet.2015.01.120

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  40 in total

1.  Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A.

Authors:  Trent Conroy; Jin T Guo; Roger G Linington; Nicholas H Hunt; Richard J Payne
Journal:  Chemistry       Date:  2011-10-18       Impact factor: 5.236

2.  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

3.  Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes.

Authors:  Travis Dudding; Ohyun Kwon; Evan Mercier
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

4.  Enantioselective Carbon-Sulfur Bond Formation: γ Additions of Aryl Thiols to Allenoates Catalyzed by a Chiral Phosphepine.

Authors:  Yuji Fujiwara; Jianwei Sun; Gregory C Fu
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

5.  A total synthesis of (-)-hemiasterlin using N-Bts methodology.

Authors:  E Vedejs; C Kongkittingam
Journal:  J Org Chem       Date:  2001-11-02       Impact factor: 4.354

6.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis.

Authors:  X Lu; C Zhang; Z Xu
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

7.  Synthesis of gamma,delta-didehydrohomoglutamates by the phosphine-catalyzed gamma-addition reaction to acetylenic esters

Authors: 
Journal:  J Org Chem       Date:  2000-06-02       Impact factor: 4.354

8.  Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.

Authors:  Rylan J Lundgren; Ashraf Wilsily; Nicolas Marion; Cong Ma; Ying Kit Chung; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-21       Impact factor: 15.336

9.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

Authors:  Xue-Feng Zhu; Jie Lan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

Review 10.  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

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  4 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.  Catalytic Enantioselective Carbon-Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C-H Bonds.

Authors:  Daniel T Ziegler; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2016-09-12       Impact factor: 15.419

3.  Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.

Authors:  Kui Zhang; Lingchao Cai; Zhongyue Yang; K N Houk; Ohyun Kwon
Journal:  Chem Sci       Date:  2018-01-18       Impact factor: 9.825

4.  Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates.

Authors:  Haile Qiu; Xiaofeng Chen; Junliang Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

  4 in total

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