21336-32-3Relevant academic research and scientific papers
General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols
Parasram, Marvin,Chuentragool, Padon,Wang, Yang,Shi, Yi,Gevorgyan, Vladimir
, p. 14857 - 14860 (2017/10/31)
A general, efficient, and site-selective visible light-induced Pd-catalyzed remote desaturation of aliphatic alcohols into valuable allylic, homoallylic, and bis-homoallylic alcohols has been developed. This transformation operates via a hybrid Pd-radical mechanism, which synergistically combines the favorable features of radical approaches, such as a facile remote C-H HAT step, with that of transition-metal-catalyzed chemistry (selective β-hydrogen elimination step). This allows achieving superior degrees of regioselectivity and yields in the desaturation of alcohols compared to those obtained by the state-of-the-art desaturation methods. The HAT at unactivated C(sp3)-H sites is enabled by the easily installable/removable Si-auxiliaries. Formation of the key hybrid alkyl Pd-radical intermediates is efficiently induced by visible light from alkyl iodides and Pd(0) complexes. Notably, this method requires no exogenous photosensitizers or external oxidants.
12-s-Cis Conformationally Locked 11cis-Retinoids: A Delineation of the Thermal Requirements for -Sigmatropic Shifts and Electrocyclizations in the Vitamin A Series and Novel Spectral Properties
Chandraratna, Roshantha, A. S.,Bayerque, Ann L.,Okamura, William H.
, p. 3588 - 3594 (2007/10/02)
The thermally induced -sigmatropic rearrangement (69 deg C, 4 h) of the six-membered ring fused vinylallenol 5b, a process specific for preparing 11-cis-retinoids, afforded 24 (12percent) and the 12-s-cis-locked retinols 11-cis-7a (14percent), 11-cis
