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Highly diastereoselective mercury-mediated synthesis of functionalized 2-azabicyclo[3.3.0]octane derivatives

✍ Scribed by Emerson P Peçanha; Hugo Verli; Carlos R Rodrigues; Eliezer J Barreiro; Carlos A.M Fraga

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
353 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

In this paper we described the synthesis of the cis-2-azabicyclo[3.3.0]octane derivative (5b) employing highly diastereoselective mercury(II)-mediated intramolecular amino-cyclization, followed by reductive demercuration of ethyl erythro-1allyl-2-amino-1-cyclopentanecarboxylate (7b). Molecular dynamic studies were performed in order to find a suitable explanation of the diastereoselectivity of azamercuration in comparison with corresponding oxymercuration process.

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