110012-76-5Relevant academic research and scientific papers
Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10
Yanagisawa,Nomura,Noritake,Yamamoto
, p. 1130 - 1136 (2007/10/02)
Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.
Palladium-Catalyzed Regio- and Stereoselective Reduction of Allylic Compounds with LiHBEt3. Application to the Synthesis of Co-enzyme Q10
Mohri, Mitsunobu,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi,Takagaki, Hidetsugu,Yamazaki, Keiji
, p. 1177 - 1180 (2007/10/02)
Regio- and stereoselective desulfonylation of allylic sulfones with LiHBEt3 in the presence of a catalytic amount of was succesfully applied to the synthesis of co-enzyme Q10.It was found that this reduction system was applicable to a wide variety of allylic functional groups.
