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Regiospecific synthesis of 6-alkyltropan-2-ones

✍ Scribed by Stacey A. Lomenzo; Amy L. Bradley; Naijue Zhu; Cheryl L. Klein; Mark L. Trudell

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
721 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new synthetic approach for the regiospecific alkylation of the 6‐position of the tropane ring system has been developed. Alkylation, desulfonylation and deprotection of tropanes 5 and 12 furnished a series of 6‐endo‐alkyltropan‐2‐one derivatives 8a‐e, 15a‐e and 16a‐e (R = Me, Et, n‐Pr, n‐Bu, Bn) stereoselectively in good yields. The 6‐endo isomers 15a‐e and 6‐exo isomers 16a‐e were easily obtained as pure diastereoisomers.

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