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Literature DB >> 21057692

The (4+3)-cycloaddition reaction: simple allylic cations as dienophiles.

Abstract

The (4+3)-cycloaddition of allylic cations to dienes is a powerful method for the direct synthesis of seven-membered rings. Recent developments in this area have included new methods for the generation of allylic cations, diastereoselective and catalytic, enantioselective reactions, an increased understanding of the diverse mechanistic possibilities of the reaction and applications to the total synthesis of natural products and their analogues.

Entities: Chemical

Year: 2010 PMID： 21057692 DOI： 10.1039/c0cc03620j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

31 in total

1. Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.

Authors: Casi M Schienebeck; Patrick J Robichaux; Xiaoxun Li; Lianqing Chen; Weiping Tang
Journal: Chem Commun (Camb) Date: 2013-04-04 Impact factor: 6.222

2. Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors: Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal: J Am Chem Soc Date: 2012-03-12 Impact factor: 15.419

3. Intramolecular oxyallyl-carbonyl (3 + 2) cycloadditions.

Authors: Elizabeth H Krenske; Shuzhong He; Jian Huang; Yunfei Du; K N Houk; Richard P Hsung
Journal: J Am Chem Soc Date: 2013-04-01 Impact factor: 15.419

4. Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors: V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal: Org Lett Date: 2020-02-03 Impact factor: 6.005

10. Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.

Authors: Yunfei Du; Elizabeth H Krenske; Jennifer E Antoline; Andrew G Lohse; K N Houk; Richard P Hsung
Journal: J Org Chem Date: 2012-07-31 Impact factor: 4.354

The (4+3)-cycloaddition reaction: simple allylic cations as dienophiles.

1. Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.

2. Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

3. Intramolecular oxyallyl-carbonyl (3 + 2) cycloadditions.

4. Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

5. Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis.

6. Synthesis of Naturally Occurring Tropones and Tropolones.

7. Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction.

8. Total synthesis of (±)-cortistatin J from furan.

9. Mechanistic Perspectives in the Regioselective Indole Addition to Unsymmetrical Silyloxyallyl Cations.

10. Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.