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

Abstract : 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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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01341576
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Submitted on : Monday, July 4, 2016 - 2:27:31 PM
Last modification on : Thursday, March 5, 2020 - 2:04:21 PM

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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, American Chemical Society, 2016, 81 (11), pp.4633--4644. ⟨10.1021/acs.joc.6b00505⟩. ⟨hal-01341576⟩

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