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Diastereoselective routes to endo and exo ethyl 1-azabicyclo[2.2.1] hept-3-YL carboxylates

✍ Scribed by Barry S. Orlek; Harry Wadsworth; Paul Wyman; Michael S. Hadley

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
218 KB
Volume
32
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES

Synthesis of ethyl 1-azabicyclo[2.2.1]he
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The dipolar cycloaddition reaction of a-methylene butyrolactone and N-benzyl azomethine ylid (5) affords the spirolactone (2) which rearranges to give ethyl 1-azabicyclo[2.2.l]hept-Cyl carboxylate (1) in excellent overall yield.

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The synthesis of the title compound (4) is described. ## Treatment of (3S)-[(lR)-hydroxyethyl]-(4R)- [ 3-(p-nitrobenzyloxy) carbonyl-2-0x0-[ 2-I4C] -3-diazopropan-l-yl]azetidin-2-one1 with rhodium diacetate achieved ring closure forming (5R,6S)-pnitrobenzyl-6-~(1R)-hydroxyethyl]-3,7-dioxo-[3-14C]