37779-25-2Relevant academic research and scientific papers
An efficient procedure for the 1,3-transposition of allylic alcohols based on lithium naphthalenide induced reductive elimination of epoxy mesylates
Wu, Yen-Ku,Liu, Hsing-Jang,Zhu, Jia-Liang
, p. 621 - 623 (2008/12/22)
An efficient protocol for the 1,3-transposition of allylic alcohols has been developed. The method is based on the pretransformation of allylic alcohols into the corresponding epoxy mesylates, followed by the reductive elimination of the resulting epoxy mesylates by using lithium naphthalenide (LN) as a reducing agent. Georg Thieme Verlag Stuttgart.
Inter- and intramolecular additions of 1-alkenylboronic acids or esters to aldehydes and ketones catalyzed by rhodium(I) complexes in basic, aqueous solutions
Takezawa, Akinori,Yamaguchi, Kenji,Ohmura, Toshimichi,Yamamoto, Yasunori,Miyaura, Norio
, p. 1733 - 1735 (2007/10/03)
Grignard-type addition reaction of 1-alkenylboronic acids or their esters to aldehydes or ketones were carried out in aqueous MeOH or DME in the presence of KOH (1 equivalent) and an RhCl(dppf) or Rh(OH)(dppf) catalyst (3 mol%). The utility of the protocol was demonstrated in the corresponding intramolecular reaction giving cyclic homoallylic alcohols.
NEW DEVELOPMENTS OF THE WHARTON TRANSPOSITION
Dupuy, C.,Luche, J. L.
, p. 3437 - 3444 (2007/10/02)
The synthetically useful Wharton transposition can be improved by using a more adequate procedure in the critical step of the intermediate α-epoxyhydrazone cleavage.Either for stable hydrazones or unstable ones, the yield of the transposed allylic alcohol is increased by treatment under anhydrous conditions with highly basic reagents (KDA in the former case, NEt3 in the latter).
