Asymmetric synthesis of aminochromanes via intramolecular indium-mediated allylation of chiral hydrazones.
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.
Samanta
Debasis
D
Department of Chemistry and Molecular Biology, North Dakota State University, Department 2735, P.O. Box 6050, Fargo, North Dakota 58108-6050, usa.
Kargbo
Robert B
RB
Cook
Gregory R
GR
D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D002839:Chromans / Q000737:chemistry*; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D008956:Models, Chemical; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000498:Allyl Compounds; D000588:Amines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002264:Carboxylic Acids; D002839:Chromans; D006835:Hydrazones; D011714:Pyrans; D007204:Indium
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