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Literature DB >> 12153260

Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides.

Xiaomei Zhang¹, Zhaohui Qu, Zhihua Ma, Weifeng Shi, Xianglin Jin, Jianbo Wang.

Abstract

Catalytic asymmetric sulfur ylide [2,3]-sigmatropic rearrangement of carbenoids generated from aryldiazoacetates has been investigated with a number of chiral Rh(II) and Cu(I) catalysts, and moderately high enantioselectivity (52-78% ee) can be achieved with Cu(MeCN)(4)PF(6)/2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline].

Entities: Chemical Gene

Year: 2002 PMID： 12153260 DOI： 10.1021/jo025687f

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

8 in total

1. Biocatalytic Synthesis of Allylic and Allenyl Sulfides through a Myoglobin-Catalyzed Doyle-Kirmse Reaction.

Authors: Vikas Tyagi; Gopeekrishnan Sreenilayam; Priyanka Bajaj; Antonio Tinoco; Rudi Fasan
Journal: Angew Chem Int Ed Engl Date: 2016-09-20 Impact factor: 15.336

2. Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.

Authors: Zhikun Zhang; Zhe Sheng; Weizhi Yu; Guojiao Wu; Rui Zhang; Wen-Dao Chu; Yan Zhang; Jianbo Wang
Journal: Nat Chem Date: 2017-06-05 Impact factor: 24.427

3. Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.

Authors: Bin Xu; Uttam K Tambar
Journal: Angew Chem Int Ed Engl Date: 2017-07-17 Impact factor: 15.336

4. Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones.

Authors: Shou-Jie Shen; Xiao-Li Du; Xiao-Li Xu; Yue-Hua Wu; Ming-Gang Zhao; Jin-Yan Liang
Journal: RSC Adv Date: 2019-10-29 Impact factor: 4.036

Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides.

1. Biocatalytic Synthesis of Allylic and Allenyl Sulfides through a Myoglobin-Catalyzed Doyle-Kirmse Reaction.

2. Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.

3. Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.

4. Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones.

Review 5. Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

Review 6. Selenonium Ylides: Syntheses, Structural Aspects, and Synthetic Applications.

7. Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens.

Review 8. Recent Perspectives on Rearrangement Reactions of Ylides via Carbene Transfer Reactions.