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Literature DB >> 24132663

Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

Anthony L Gerten¹, Michael C Slade, Kelsie M Pugh, Levi M Stanley.

Abstract

Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones are reported. The spiro[pyrazolin-3,3'-oxindole] products are formed in good yields (up to 98%) and high enantioselectivity (up to 99% ee).

Entities: Chemical Gene

Mesh：

Substances：

Year: 2013 PMID： 24132663 PMCID： PMC3876797 DOI： 10.1039/c3ob41815d

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

17 in total

1. Catalytic asymmetric exo'-selective [3+2] cycloaddition for constructing stereochemically diversified spiro[pyrrolidin-3,3'-oxindole]s.

Authors: Atsuko Awata; Takayoshi Arai
Journal: Chemistry Date: 2012-06-11 Impact factor: 5.236

2. Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products.

Authors: Andrey P Antonchick; Claas Gerding-Reimers; Mario Catarinella; Markus Schürmann; Hans Preut; Slava Ziegler; Daniel Rauh; Herbert Waldmann
Journal: Nat Chem Date: 2010-07-11 Impact factor: 24.427

3. Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition.

Authors: Barry M Trost; Nicolai Cramer; Steven M Silverman
Journal: J Am Chem Soc Date: 2007-09-20 Impact factor: 15.419

4. Highly enantioselective [3+2] annulation of Morita-Baylis-Hillman adducts mediated by L-threonine-derived phosphines: synthesis of 3-spirocyclopentene-2-oxindoles having two contiguous quaternary centers.

Authors: Fangrui Zhong; Xiaoyu Han; Youqing Wang; Yixin Lu
Journal: Angew Chem Int Ed Engl Date: 2011-07-04 Impact factor: 15.336

5. Organocatalytic synthesis of spiro[pyrrolidin-3,3'-oxindoles] with high enantiopurity and structural diversity.

Authors: Xiao-Hua Chen; Qiang Wei; Shi-Wei Luo; Han Xiao; Liu-Zhu Gong
Journal: J Am Chem Soc Date: 2009-09-30 Impact factor: 15.419

6. An entry to a chiral dihydropyrazole scaffold: enantioselective [3 + 2] cycloaddition of nitrile imines.

Authors: Mukund P Sibi; Levi M Stanley; Craig P Jasperse
Journal: J Am Chem Soc Date: 2005-06-15 Impact factor: 15.419

7. Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines.

Authors: Liang Hong; Ming Kai; Chongyang Wu; Wangsheng Sun; Gongming Zhu; Guofeng Li; Xiaojun Yao; Rui Wang
Journal: Chem Commun (Camb) Date: 2013-08-04 Impact factor: 6.222

8. Biomimetic asymmetric 1,3-dioplar cycloaddition: amino acid precursors in biosynthesis serve as latent azomethine ylides.

Authors: Chang Guo; Jin Song; Liu-Zhu Gong
Journal: Org Lett Date: 2013-05-16 Impact factor: 6.005

2. Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center.

Authors: Bo Chen; Wen-Dao Chu; Quan-Zhong Liu
Journal: RSC Adv Date: 2019-01-11 Impact factor: 4.036

2 in total