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Literature DB >> 16248627

Highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and sulfides.

Ming Ma¹, Lingling Peng, Changkun Li, Xiu Zhang, Jianbo Wang.

Abstract

A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and allyl and propargyl sulfides by a double asymmetric induction approach that combines a chiral camphor sultam auxiliary and Cu(I) catalyst with chiral or achiral diimine ligands has been developed.

Entities: Chemical

Year: 2005 PMID： 16248627 DOI： 10.1021/ja055021d

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

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Cited

12 in total

1. Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

Authors: Matthew Hassink; Xiaozhong Liu; Joseph M Fox
Journal: Org Lett Date: 2011-04-12 Impact factor: 6.005

2. 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

3. 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

4. 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

5. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors: Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal: Chem Rev Date: 2019-06-25 Impact factor: 60.622

6. Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Authors: Zhanjie Li; Brendan T Parr; Huw M L Davies
Journal: J Am Chem Soc Date: 2012-06-25 Impact factor: 15.419

Review 7. Acyclic Twisted Amides.

Authors: Guangrong Meng; Jin Zhang; Michal Szostak
Journal: Chem Rev Date: 2021-08-18 Impact factor: 72.087