58958-05-7

Upstream product

• 57566-86-6 (2Ξ,4R)-4-hydroxy-6-methyl-2-(phenylselanyl-methyl)-heptanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 128291-28-1 2'-isopropenylpotassium 
• 590-86-3 isovaleraldehyde 
• 128291-26-9 B-isoprenyldiisopinocampheylborane 
• 62961-64-2 D-(-)-diisopropyl tartrate 
• 122038-72-6 dimethoxyisoprenylborane 
• 1826-67-1 vinyl magnesium bromide 
• 57566-87-7 (R)-5-Isobutyl-3-phenylselanylmethyl-dihydro-furan-2-one 
• 123-51-3 i-Amyl alcohol 
• 1335316-66-9 4,4,5,5-tetramethyl-2-(2-methylenebut-3-enyl)-1,3,2-dioxaborolane 
• 60856-89-5 2-(R)-isobutyl-oxirane 
• 32657-89-9 1,3-butadien-2-ylmagnesium chloride 

Relevant academic research and scientific papers

Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid

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.).

Enantioselective iridium-catalyzed carbonyl isoprenylation: Via alcohol-mediated hydrogen transfer

Highly enantioselective iridium catalyzed carbonyl (2-vinyl)allylation or "isoprenylation" is achieved via hydrogen auto-transfer or 2-propanol-mediated reductive coupling from primary alcohol or aldehyde reactants, respectively. Using this method, asymmetric total syntheses of the terpenoid natural products (+)-ipsenol and (+)-ipsdienol were achieved.

Enantioselective synthesis of ipsenol and ipsdienol using a (2-bromoallyl)borane derivative

(S)-(-)-Ipsenol and (S)-(+)-ipsdienol, a major component of the sex pheromone of the bark beetle, and their enantiomers were prepared enantioselectively using tartrate esters of (2-bromoallyl)boronic acid in the key step.

Intermediates useful for the chiral isoprenylation of aldehydes

An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol. This invention also concerns novel intermediates R'2 B(2'-isoprenyl) wherein R' is isopinocampheyl, 2-isocaranyl and 4-isocaranyl.

Chiral synthesis VIA organoboranes. 26. An efficient synthesis of isoprenyl derivatives of borane - Valuable reagents for the isoprenylboration of aldehydes. A convenient route to both enantiomers of ipsenol and ipsdienol in high optical purity

Preparation of B-isoprenyldialkylboranes is achieved by adopting the Brandsma modification of the Schlosser procedure, namely metallation of isoprene with potassium 2,2,5,5-tetramethylpiperidide followed by sequential treatment with 5-methoxydialkylborane and boron trifluoride-etherate. These reagents are used for the convenient isoprenylation of aldehydes. Reaction of isovaleraldehyde and β, β-dimethylacrolein with B2′isoprenyldiisopinocampheylborane provides both ipsenol and ipsdienol, respectively in 65% yields and 96% ee.

B-2'-ISOPRENYLDIISOPINOCAMPHEYLBORANE: AN EFFICIENT REAGENT FOR THE CHIRAL ISOPRENYLATION OF ALDEHYDES. A CONVENIENT ROUTE TO BOTH ENANTIOMERS OF IPSENOL AND IPSDIENOL

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.