[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

[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

Domains: Chemical Sciences; Organic chemistry

Sabrina Touchet, Aurélie Macé, Thierry Roisnel, François Carreaux, Alexandre Bouillon, et al.. [3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans.. Organic Letters, 2013, 15 (11), pp.2712-5. ⟨10.1021/ol401016x⟩. ⟨hal-00861083⟩