Tandem InCl3-Promoted Hydroperoxide Rearrangements and Nucleophilic Additions: A Straightforward Entry to Benzoxacycles

被引：4

作者：

Bosnidou, Alexandra E. E. ^{[1
]}

Fayet, Agathe ^{[1
,2
]}

Cheibas, Cristina ^{[1
]}

Gayraud, Oscar ^{[1
]}

Bourcier, Sophie ^{[3
]}

Frison, Gilles ^{[2
]}

Nay, Bastien ^{[1
]}

机构：

[1] Inst Polytech Paris, Ecole Polytech, Lab Syntheese Organ, CNRS,ENSTA, F-91128 Palaiseau, France

[2] Sorbonne Univ, CNRS, Lab Chim Theeor, F-75005 Paris, France

[3] Inst Polytech Paris, Ecole Polytech, Lab Chim Mol, CNRS, F-91128 Palaiseau, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期

关键词：

ACID; PEROXIDES; CHEMISTRY; ALKENES; ETHERS; ESTERS; 5-HT1A;

D O I：

10.1021/acs.joc.3c00845

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Theacid-catalyzed rearrangement of organic peroxides is generallyassociated with C-C-bond cleavages (Hock and Criegee rearrangements),with the concomitant formation of an oxocarbenium intermediate. Thisarticle describes the tandem process between a Hock or Criegee oxidativecleavage and a nucleophilic addition onto the oxocarbenium species(in particular a Hosomi-Sakurai-type allylation), under InCl3 catalysis. It was applied to the synthesis of 2-substitutedbenzoxacycles (chromanes and benzoxepanes), including a synthesisof the 2-(aminomethyl)chromane part of sarizotan, and a total synthesisof erythrococcamide B.

引用

页码：9277 / 9282

页数：6

共 19 条

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