Stereospecific Synthesis of α-Amino Allylsilane Derivatives through a [3,3]-Allyl Cyanate Rearrangement. Mild Formation of Functionalized Disiloxanes - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2016

Stereospecific Synthesis of α-Amino Allylsilane Derivatives through a [3,3]-Allyl Cyanate Rearrangement. Mild Formation of Functionalized Disiloxanes

Résumé

An efficient asymmetric synthesis of α-amino allylsilane derivatives is reported. The strategy is based on a [3,3]-allyl cyanate sigmatropic rearrangement from enantioenriched γ-hydroxy alkenylsilyl compounds. The isocyanate intermediate can be trapped by several nucleophiles, opening the way for the preparation of unknown chiral functionalized compounds such as the α-ureido allylsilanes as well as carbamate derivatives. A computational study was conducted to rationalize the complete 1,3-chirality transfer of this kind of rearrangement. Moreover, starting from products bearing a phenyldimethyl silyl substituent, the α-amino silane derivatives or the corresponding disiloxanes can be obtained under hydrogenation conditions in an exclusive way according to the used catalyst. © 2016 American Chemical Society.
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Dates et versions

hal-01341576 , version 1 (04-07-2016)

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Citer

S. Henrion, B. Carboni, F.P. Cossio, T. Roisnel, J.M. Villalgordo, et al.. Stereospecific Synthesis of α-Amino Allylsilane Derivatives through a [3,3]-Allyl Cyanate Rearrangement. Mild Formation of Functionalized Disiloxanes. Journal of Organic Chemistry, 2016, 81 (11), pp.4633--4644. ⟨10.1021/acs.joc.6b00505⟩. ⟨hal-01341576⟩
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