(3+3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

被引：31

作者：

Cordier, Marie ^{[1
]}

Archambeau, Alexis ^{[2
]}

机构：

[1] Ecole Polytech, CNRS, UMR 9168, Lab Chim Mol, F-91128 Palaiseau, France

[2] Ecole Polytech, CNRS, UMR 9168, Lab Synth Organ,ENSTA ParisTech, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 08期

关键词：

AZOMETHINE IMINES; FACILE ACCESS; N-OXIDES; KETONES; TRIMETHYLENEMETHANE; CYCLOPROPANES; INTERMEDIATE; GENERATION; ADDITIONS; FURAN;

D O I：

10.1021/acs.orglett.8b00617

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxyallyl cations are prepared in situ from readily available a-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

引用

页码：2265 / 2268

页数：4

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