Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones-Reference-Cited by-同舟云学术

Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones

Published:2000 Issue:5 Volume:65 Page:708-716
ISSN:0010-0765
Container-title:Collection of Czechoslovak Chemical Communications
language:en
Short-container-title:Collect. Czech. Chem. Commun.

Author:

Častulík Jakub,Jonas Jaroslav,Mazal Ctibor

Abstract

The nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine adds to both isomers of 3-(tosyloxymethylene)tetrahydrofuran-2-one with excellent regio- and stereoselectivity giving spiroheterocyclic products in moderate yields. X-Ray structure determination showed dibutolactone to have the E-configuration; the corresponding Z-isomer was prepared photochemically.

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

Cited by 4 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Substituent Effect on exo Stereoselectivity in the 1,3-Dipolar Cycloaddition Reaction of Tulipalin A with Nitrile Ylides;The Journal of Organic Chemistry;2008-03-20

2. π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position;Collection of Czechoslovak Chemical Communications;2002

3. Synthesis of spiropyrrolidines and spiropyrrolizidines by 1,3-dipolar cycloadditions of azomethine ylides to substituted α-methylene-γ-lactones;Tetrahedron;2001-09

4. ChemInform Abstract: Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones.;ChemInform;2000-09-12