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247. Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols.

Author

do Rego Barros, Olga Soares, Sirvent, Juan Alberto, Foubelo, Francisco, and Yus, Miguel

Subjects
STEREOSELECTIVE reactions, ALLYLATION, BUTENOL, IMINE synthesis, ALLYL alcohol, PALLADIUM catalysts
Abstract

The palladium-catalyzed allylation of N-tert-butanesulfinyl imines with allylic alcohols in the presence of InI as reducing reagent takes place with high diastereoselectivity in reasonable yields. The reaction with crotyl alcohol is totally regioselective, leading to the antidiastereomer as the main reaction product. [ABSTRACT FROM AUTHOR]

Published
2014
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248. Diastereoselective Indium-Promoted Allylation of Chiral N-Sulfinyl Imines.

Author

Foubelo, Francisco and Yus, Miguel

Subjects
*INDIUM, *GROUP 13 elements, *ALLYLATION, *SULFINYL compounds, *ORGANOSULFUR compounds
Abstract

The indium-promoted allylation of enantiomerically pure N- tert-butylsulfinyl imines has been shown to be a versatile and useful methodology for the preparation of diastereomerically enriched N-protected homoallylamines. The preparation of both enantiomeric diastereomers is possible by changing the stereochemistry of the starting imine. Importantly, the deprotection of the sulfinylamines is easily achieved by acid treatment, and, therefore, the corresponding free amines are accessible in an enantioenriched manner. This methodology has been applied to the synthesis of interesting compounds, that is, mostly alkaloids and a wide representation of naturally occurring products. [ABSTRACT FROM AUTHOR]

Published
2014
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