[3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans.

Sabrina Touchet; Aurélie Macé; Thierry Roisnel; François Carreaux; Alexandre Bouillon; Bertrand Carboni

doi:10.1021/ol401016x

Journal articles

[3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans.

Sabrina Touchet ¹ Aurélie Macé ¹ Thierry Roisnel ¹ François Carreaux ¹ Alexandre Bouillon Bertrand Carboni ¹

1 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : [3,3]-Sigmatropic cyanate-isocyanate rearrangement provides a powerful tool for the preparation of α-isocyanato allylboronic esters, which can be further trapped with a variety of nucleophiles. Hydrogenation gave the corresponding α-aminoboronates derivatives while addition of aldehydes afforded homoallylic alcohols, (tetrahydrofuran-2-yl)carbamate, ether, or urea derivatives.

Keywords : cyanate rearrangement boronic isocyanate aminoboronic homoallylic alcohols tetrahydrofuran carbamate ether urea

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Journal articles

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Chemical Sciences / Organic chemistry

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-00861083
Contributor : Bertrand Carboni <>
Submitted on : Wednesday, September 11, 2013 - 6:30:03 PM
Last modification on : Friday, July 10, 2020 - 4:24:32 PM

[3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans.

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[3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans.

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