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Synlett 1995; 1995(3): 237-238
DOI: 10.1055/s-1995-4922
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Cyclisation/Rearrangement of L-Serine-derived Diazoesters: Synthesis of Enantiomerically Pure 1,3,4,6,11,11a-Hexahydro[1,4]oxazino[4,3-b]isoquinolines

Florencio Zaragoza*
  • *Technische Universität Dresden, Institut für Organische Chemie, Mommsenstraße 13, D-01062 Dresden, Germany
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Publication Date:
31 December 2000 (online)

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Diazoesters 1a,b were synthesized in four steps from L-serine methyl ester hydrochloride (4). Their rhodium(II) acetate catalysed decomposition furnished the tetrahydroisoquinoline-derivatives 3a and 3b.

dihydroisoindole - rhodium(II) carbenoide - L-serine - Stevens rearrangement - tetrahydroisoquinoline-3-carboxylic ester