86372-74-9Relevant academic research and scientific papers
Catalytic asymmetric allylic transfer reactions for the Enantioselective synthesis of dienyl and enynyl alcohols
Yu, Chan-Mo,Jeon, Miyoo,Lee, Jae-Young,Jeon, Junha
, p. 1143 - 1148 (2001)
Efficient catalytic asymmetric allylic transfer reactions of achiral aldehydes with 2-ethynyl- and 2-ethenyl-2-propenyl-stannane promoted by BINOL-TiIV complex with synergetic reagent are achieved for the synthesis of homoenynyl- and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84-99% ee with good chemical yields. The application of catalytic asymmetric dienylation in a single operation was exemplified by the enantioselective synthesis of naturally occurring (-)-Ipsdienol and (-)-Ipsenol.
Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid
Zhang, Yu-Long,He, Bo-Jun,Xie, Yi-Wen,Wang, Yu-Hao,Wang, Yi-Long,Shen, Yong-Cun,Huang, Yi-Yong
supporting information, p. 3074 - 3079 (2019/05/15)
The BINOL-derived chiral phosphoric acid (R)-TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen-bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including two natural products (?)-Ipsdienol and (?)-Ipsenol, have been successfully constituted. The synthetic application to chiral isoprenylated isobenzofuranone, vinyloxirane and cyclohexene derivatives has also been disclosed. (Figure presented.).
B-2'-ISOPRENYLDIISOPINOCAMPHEYLBORANE: AN EFFICIENT REAGENT FOR THE CHIRAL ISOPRENYLATION OF ALDEHYDES. A CONVENIENT ROUTE TO BOTH ENANTIOMERS OF IPSENOL AND IPSDIENOL
Brown, Herbert C.,Randal, Ramnarayan S.
, p. 455 - 458 (2007/10/02)
B-2'-Isoprenyldiisopinocampheylborane is prepared by metallation of isoprene with potassium 2,2,5,5-tetramethylpiperidide followed by sequential treatment with B-methoxydiisopinocampheylborane and boron trifluoride-etherate.Condensation of this reagent with aldehydes provides isoprenylated chiral alcohols.This methodology is utilized for an efficient one-pot synthesis of both enantiomers of the pheromones of the bark beetle Ips paraconfusus Lanier, ipsenol and ipsdienol in 96percent ee and 65percent isolated yields.
