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Synthesis applications of aza-cope rearrangements.: Stereocontrolled synthesis of cyclohepta [b]pyroolidines1

✍ Scribed by Larry E Overman; E.Jon Jacobsen

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 226 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87445-6

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✦ Synopsis

pyrroles can be prepared in stereocontrolled fashions by the reaction of 2-amino-l-(l-phenylvlnyl)cyclohexanols with formaldehyde and acid.

Recent papers from our laboratory have described the use of "Mannich-directed" cationic aza-Cope rearrangements for the preparation of octahydroindolones by an unusual ring-enlarging pyrrolrdlne annulation reaction (eq 1, n=l). lr2 In this Letter, we report that the analogous rearrangement of cyclohexanols provides a convenient entry to cyclohepta[b]pyrrolidlnes (eq 1, n=2).

This ring system, 3 although not common, is found in several natural products, for example, the antihypertensive alkaloid gelsemlne. 4

We moreover report that the ring-

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