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Synlett 1996; 1996(8): 781-782
DOI: 10.1055/s-1996-5528
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Neighbouring Group Assistance in the Formation of Phthalimidines from o-Phthalaldehyde: an ”Intramolecular Auxiliary Effect”

Steven M. Allin* , Claire C. Hodkinson, Navid Taj
  • *Department of Chemical & Biological Sciences, The University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, England, FAX: 44 1484 472182, EMAIL: s.m.allin@hud.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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The reaction of o-phthalaldehyde with α-amino acids (and amino alcohols) proceeds efficiently in acetonitrile to give the corresponding phthalimidines in good yield. The presence of external ”synthetic auxiliaries” is unnecessary. A mechanism involving neighbouring group assistance by the acid (or alcohol) group is proposed.

monoimine - oxazolidinone - isoindolinol - phthalimidine

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