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0342637873
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note
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The regioisomer 7 was formed as a by-product (approx. 10% yield). Reduction of the aziridinium intermediate depicted in the figure accounts for its formation. (matrix presented)
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For the synthesis of enantiopure cis-fused 2-substituted octahydroindol-6-ones, bearing a 2-carboxylic acid substituent at C-2, see: Bonjoch, J.; Catena, J.; Isábal, E.; López-Canet, M.; Valls, N. Tetrahedron: Asymmetry 1996, 7, 1899-1902.
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23
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0025234942
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For studies on the regioselectivity and isomerization processes in the Fischer indolization of β-amino ketones, see: Bonjoch, J.; Casamitjana, N.; Gràcia, J.; Úbeda, M.-C.; Bosch, J. Tetrahedron Lett. 1990, 31, 2449-2452.
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0014531898
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For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
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Ban, Y.1
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0017373420
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For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
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0342637871
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For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
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0040483232
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For a discussion about the stereochemical factors influencing the regiochemical course of Fischer indole synthesis, see: Freter, K.; Fuchs, V.; Pitner, T. P. J. Org. Chem. 1983, 48, 4593-4597. See also, Hugues, D. L.; Zhao, D. J. Org. Chem. 1993, 58, 228-233.
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0000414271
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