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Asymmetric synthesis of aminochromanes via intramolecular indium-mediated allylation of chiral hydrazones.

ABSTRACT: The asymmetric intramolecular indium-mediated cyclization reaction delivers chromanes with excellent diastereoselectivity (68-91% yield, dr >99:1). The reaction was efficient for aryl substrates with both electron-withdrawing and -donating groups. Carboxylic acid additives were found to be necessary for optimal reaction.

SUBMITTER: Samanta D

PROVIDER: S-EPMC6280656 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of aminochromanes via intramolecular indium-mediated allylation of chiral hydrazones.

Samanta Debasis D Kargbo Robert B RB Cook Gregory R GR

The Journal of organic chemistry 20090901 18

The asymmetric intramolecular indium-mediated cyclization reaction delivers chromanes with excellent diastereoselectivity (68-91% yield, dr >99:1). The reaction was efficient for aryl substrates with both electron-withdrawing and -donating groups. Carboxylic acid additives were found to be necessary for optimal reaction. ...[more]

PMID: 19702255

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