Stereoselective Syntheses of cis- and trans-2-Alkylamino-1, 2, 3, 4-tetrahydro-1-naphthalenols by Acid-catalyzed Ring Opening of 1, 2-N-Alkylimino-1, 2, 3, 4-tetrahydronaphthalenes

Abstract

5- or 7-Substituted cis- and trans-2-tert-butylamino-6-hydroxy-1, 2, 3, 4-tetrahydro-1-naphthalenols (cis-29-cis-32) and (trans-30-trans-35) were synthesized from 1, 2-N-tertbutylimino derivatives. Acid-catalyzed ring opening of 1, 2-alkylimino-1, 2, 3, 4-tetrahydronaphthalene derivatives (1-11) produced a mixture of cis- and trans-2-alkylamino-1, 2, 3, 4-tetrahydro-1-naphthalenol derivatives whose ratio was markedly affected by substituents on the benzene ring. Stereoselective ring opening of the aziridines and interconversion of cis- and trans-2-alkylamino-1-tetralols via 1-hydroxysulfonyloxy intermediates were described. The reaction mechanism of acid-catalyzed ring opening of the aziridines and hydrolysis of 2-alkylamino-1-hydroxysulfonyloxy-1, 2, 3, 4-tetrahydronaphthalene derivatives is also discussed.