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Literature DB >> 12733892

Broad-spectrum radical cyclizations boosted by polarity matching. Carbonylative access to alpha-stannylmethylene lactams from azaenynes and CO.

Ilhyong Ryu¹, Hironari Miyazato, Hiroki Kuriyama, Kazutoshi Matsu, Mami Tojino, Takahide Fukuyama, Satoshi Minakata, Mitsuo Komatsu.

Abstract

Free-radical mediated stannylcarbonylation of azaenynes provides a general [n + 1]-type annulation approach leading to alpha-stannylmethylene lactams. The cyclization is unusual in its breadth, covering 4-exo, 5-exo, 6-exo, 7-exo, and 8-exo modes.

Entities: Chemical

Year: 2003 PMID： 12733892 DOI： 10.1021/ja034896u

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

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Cited

6 in total

1. Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.

Authors: Seth W Grant; Koudi Zhu; Yu Zhang; Steven L Castle
Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005

2. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

Authors: Li Cui; Longwu Ye; Liming Zhang
Journal: Chem Commun (Camb) Date: 2010-03-30 Impact factor: 6.222

3. Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp³)-H functionalization.

Authors: Yang Li; Gao-Hui Pan; Ming Hu; Bang Liu; Ren-Jie Song; Jin-Heng Li
Journal: Chem Sci Date: 2016-07-21 Impact factor: 9.825

Broad-spectrum radical cyclizations boosted by polarity matching. Carbonylative access to alpha-stannylmethylene lactams from azaenynes and CO.

1. Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.

2. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

3. Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp³)-H functionalization.

Review 4. Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.

5. Radical carbonylations using a continuous microflow system.

6. A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide.

Broad-spectrum radical cyclizations boosted by polarity matching. Carbonylative access to alpha-stannylmethylene lactams from azaenynes and CO.

1. Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.

2. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

3. Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp3)-H functionalization.

Review 4. Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.

5. Radical carbonylations using a continuous microflow system.

6. A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide.

3. Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp³)-H functionalization.