Literature DB >> 19485325

A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric alpha-addition of isocyanides to aldehydes.

Hisashi Mihara1, Yingjie Xu, Nicholas E Shepherd, Shigeki Matsunaga, Masakatsu Shibasaki.   

Abstract

Development of a new heterobimetallic Ga(O-iPr)(3)/Yb(OTf)(3)/Schiff base 2d complex for catalytic asymmetric alpha-additions of isocyanides to aldehydes is described. Schiff base 2d derived from o-vanillin was suitable to utilize cationic rare earth metal triflates with good Lewis acidity in bimetallic Schiff base catalysis. The Ga(O-iPr)(3)/Yb(OTf)(3)/Schiff base 2d complex promoted asymmetric alpha-additions of alpha-isocyanoacetamides to aryl, heteroaryl, alkenyl, and alkyl aldehydes in good to excellent enantioselectivity (88-98% ee).

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Year:  2009        PMID： 19485325     DOI： 10.1021/ja903158x

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


  10 in total

Review 1.  Chemistry and biology of multicomponent reactions.

Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

2.  Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO,O'}tris-(thio-cyanato-κN)europium(III).

Authors:  Jian-Feng Liu; Jia-Lu Liu; Guo-Liang Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-21

3.  C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.

Authors:  Ming Shang; Jessica Z Chan; Min Cao; Yejin Chang; Qifan Wang; Brennan Cook; Sebastian Torker; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2018-08-10       Impact factor: 15.419

4.  An Efficient Boric Acid Mediated Preparation of α-Hydroxyamides.

Authors:  J Sravan Kumar; Subash C Jonnalagadda; Venkatram R Mereddy
Journal:  Tetrahedron Lett       Date:  2010-02-03       Impact factor: 2.415

5.  A N,N'-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates.

Authors:  Weiwei Luo; Xiao Yuan; Lili Lin; Pengfei Zhou; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-04-22       Impact factor: 9.825

6.  Catalytic asymmetric 1,4-additions of beta-keto esters to nitroalkenes promoted by a bifunctional homobimetallic Co2-Schiff base complex.

Authors:  Makoto Furutachi; Zhihua Chen; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Molecules       Date:  2010-01-22       Impact factor: 4.411

7.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

Review 8.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

9.  Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction.

Authors:  Achille Antenucci; Francesco Marra; Stefano Dughera
Journal:  RSC Adv       Date:  2021-07-29       Impact factor: 4.036

10.  Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis.

Authors:  Takayoshi Arai; Katsuya Sato; Ayu Nakamura; Hiroki Makino; Hyuma Masu
Journal:  Sci Rep       Date:  2018-01-16       Impact factor: 4.379
  10 in total

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