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The cyanomethyl group for nitrogen protection and iminium ion generation in ring-enlarging pyrrolidine annulations. A short synthesis of the amaryllidaceae alkaloid d,1-crinine

✍ Scribed by Larry E Overman; E.Jon Jacobsen


Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
199 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis


The preparation of cis-3a-aryl-4-oxo-decahydrocyclohepta[b]pyrroles and cis-3a-aryl-4-oxo-octahydroindoles is facilitated by using a cyanomethyl group to both protect nitrogen and serve as a precursor for a formaldehyde imlnlum ion.

Recent publications from our laboratory have described the efficient forma-