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Aza [3.1.1] propellane durch diels-alder-addition von bicyclo [1.1.0] but-1 (3)-en-derivaten an isoindole

✍ Scribed by Hans-Georg Zoch; Arnulf-Dieter Schlüter; Günter Szeimies


Book ID
104242512
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
192 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis


The reaction of the halobicyclobutane derivatives f and 2 with LDA in the = presence of isoindoles afforded the azapropellanes 4 and 2 via the bicyclobutene intermediates 2 and ,7, respectively.


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✍ Eric D. Moher 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 192 KB

The first preparation of enantiomerically pure bicyclo[3.1.0]hexane-2-one-6-carboxylic acid ethyl ester (1), a valuable synthetic intermediate, is described. The synthesis features a retro-Diels-Alder reaction as a key step. Conditions which allow for a high yielding thermal conversion of 3 to 4 are