[3,3]-Sigmatropic rearrangement of boronated allylcyanates: a new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans. - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2013

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

(1) , (1) , (1) , (1) , , (1)
1
Aurélie Macé
Alexandre Bouillon
  • Function : Author
Bertrand Carboni
  • Function : Author
  • PersonId : 930674

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.
Not file

Dates and versions

hal-00861083 , version 1 (11-09-2013)

Identifiers

Cite

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⟩
67 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More