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Literature DB >> 20014802

Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: application to selective three-component reaction with 1,3-diynes.

Ryu Yamasaki¹, Natsuki Terashima, Ikuo Sotome, Shunsuke Komagawa, Shinichi Saito.

Abstract

Heteroatom-substituted alkynes such as ynol ethers and ynamines turned out to be decent substrates for the Ni-catalyzed [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate (1). The three-component cocyclization of 1, 1,3-diynes, and heteroatom-substituted alkynes also proceeded selectively. The study provided an efficient method for the synthesis of heteroatom-substituted cycloheptadiene and related compounds.

Entities: Chemical

Year: 2010 PMID： 20014802 DOI： 10.1021/jo902251m

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

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Cited

8 in total

1. An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors: Kyle A Dekorver; Troy D North; Richard P Hsung
Journal: Synlett Date: 2010-10 Impact factor: 2.454

Review 2. Ynamides: a modern functional group for the new millennium.

Authors: Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2010-09-08 Impact factor: 60.622

3. Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors: Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal: J Am Chem Soc Date: 2011-08-03 Impact factor: 15.419

4. N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors: Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal: J Org Chem Date: 2011-05-24 Impact factor: 4.354

Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: application to selective three-component reaction with 1,3-diynes.

1. An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Review 2. Ynamides: a modern functional group for the new millennium.

3. Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

4. N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

5. Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides.

6. Synthesis of 2-iodoynamides and regioselective [2+2] cycloadditions with ketene.

7. Ynamides in ring forming transformations.

Review 8. Preparation and Utility of N-Alkynyl Azoles in Synthesis.