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2005
Isoquinoline derivatives
R 0420
Intramolecular Diels—Alder Reaction of 4-(N-Furfuryl)aminobut-1-enes. New
to the Synthesis of 6,8a-Epoxyoctahydroisoquinoline (3-Aza-11-oxatri02- 142 Approach
cyclo[6.2.1.01,6]undec-9-ene) Derivatives. — A new one-step method for the synthesis of title epoxyoctahydroisoquinoline derivatives (VII) and (IX) is presented, involving the intramolecular cycloaddition reaction of homoallylamines (IV) and (VIII),
resp., in the presence of N-acylating agents. The cycloaddition reaction proceeds with
exo-stereoselectivity. The influence of N-acylating agent on the yield is studied but no
clear trend can be found. The reaction does not proceed with homomethallyl analogues
probably due to steric hindrance at the homoallylic double bond. — (ZUBKOV*, F.
I.; NIKITINA, E. V.; TURCHIN, K. F.; SAFRONOVA, A. A.; BORISOV, R. S.;
VARLAMOV, A. V.; Russ. Chem. Bull. 53 (2004) 4, 860-872; Russ. Peoples'
Friendship Univ., Moscow 117198, Russia; Eng.) — Mischke
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