103561-12-2Relevant academic research and scientific papers
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
WITTIG AND HORNER-WITTIG COUPLING REACTIONS OF 2-SUBSTITUTED CYCLIC ETHERS AND THEIR APPLICATION TO SPIROKETAL SYNTHESIS
Ley, Steven V.,Lygo, Barry,Organ, Helen M.,Wonnacott, Anne
, p. 3825 - 3836 (2007/10/02)
Wittig and Horner-Wittig coupling reactions of tetrahydropyran or tetrahydrofuran 2-triphenylphosphonium salts or 2-diphenylphosphine oxides with aldehydes and lactols affords good yields of the corresponding enol ethers.In selected examples these enol ether products may be further converted to spiroketals some of which are natural pheromones derived from Dacus oleae and Paravespula vulgaris.
