69668-89-9Relevant academic research and scientific papers
A NOVEL REACTION OF α-HALOEPOXIDES WITH TRIALKYLSTANNATES
Corey, L. D.,Singh, S. M.,Oehlschlager, A. C.
, p. 1821 - 1827 (2007/10/02)
The reaction of α-haloepoxides with zinc powder or reagents containing tialkylstannate anion yields allylic alcohols by anti elimination of carbon halogen and adjacent carbon epoxy oxygen bonds.Appreciable Z -> E isomerization occurs in both types of reactions but the experimental results indicate that the conversion of erythro α-bromoepoxides to E allylic alcohols by zinc or trialkylstannates shows sufficient sterospecificity to be synthetically useful.
STEREO- AND REGIOSELECTIVITY IN IODO DIOL FORMATION FROM ACYCLIC ALLYLIC ALCOHOLS
Chamberlin, A. Richard,Mulholland, Robert L.
, p. 2297 - 2302 (2007/10/02)
Reaction of electrophiles with a variety of acyclic allylic alcohols was investigated.Both aqueous iodine and acetylhypoiodite convert certain alkenols into iodo diols and acetoxy iodo alcohols, respectively, with regio- and stereoselectivities as high as 99percent.Protection of alcohol group lowers the selectivity only slightly.Structural factors that control the regioselectivity of iodohydrin formation in these substrates have been delineated.Some of the iodo diols have been deiodinated, illustrating a simple two step procedure for converting allylic alcohols into threo-1,3-diols.
