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Nickel and Palladium Catalysis in the Stereoselective Synthesis of Functionalized Pyrrolidines: Enantioselective Formal Synthesis of (+)-α-Allokainic Acid

✍ Scribed by Maxim V. Chevliakov; John Montgomery

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 110 KB
Volume: 37
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19981204)37:22<3144::aid-anie3144>3.0.co;2-y

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✦ Synopsis

Neuroexcitatory natural products are accessible from 1 via the intermediate 2, which is obtained by Ni-catalyzed cyclization, transposition of the protecting group, and Pd-catalyzed reduction with allylic transposition. This stepwise formation of stereocenters allows a highly direct and stereoselective synthesis of the excitatory amino acid (+)-α-allokainic acid, which displays an all-trans arrangement of the substituents about the pyrrolidine ring. TBS=tert-butyldimethylsilyl.

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