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A Synthesis of Enantiomerically Pure Benzoxazine and Tetrahydroquinoline Derivatives from a Chiral Aziridine : A Formal Synthesis of (-)-Swainsonine from a Chiral Aziridine

초록/요약

A synthesis of enantiomerically pure 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine and 2-hydroxymethyl-1,2,3,4-tetrahydroquinoline derivatives was successfully achieved via a palladium-catalyzed intramolecular bond formation between the nitrogen originated from aziridine and the halogenated aromatic carbon.

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초록/요약

Eanatiomerically pure (-)-swainsonine was synthesized efficiently from chiral aiziridine-2-carboxylate using mesylation and intramolecular cyclization.

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