64726-93-8Relevant academic research and scientific papers
Synthetic Applications of the Enantioselective Reduction by Binaphthol-Modified Lithium Aluminum Hydride Reagents
Noyori, R.,Tomino, I.,Yamada, M.,Nishizawa, M.
, p. 6717 - 6725 (1984)
The reduction of prochiral carbonyl substrates with the chiral binaphthol-modified lithium aluminum hydride reagents provides an effective means for preparing alcoholic products of high optical purity.The reaction is applicable to a variety of structurally diverse unsaturated carbonyl compounds such as aromatic ketones, acetylenic ketones, olefinic ketones and aldehydes, etc.Either of the antipodes is obtainable in a predictable manner by choosing the handedness of the auxiliary binaphthol ligand.The utility is exemplified by the efficiently stereocontrolled synthesis of prostaglandin intermediates, some insect pheromones, chiral primary terpenic alcohols, optically active styrene oxide, etc.
Synthesis of Optically Pure (R,Z)-5-Dec-1-enyloxacyclopentan-2-one, the Sex Pheromone of the Japanese Beetle
Baker, Raymond,Rao, V. Bhaskar
, p. 69 - 72 (2007/10/02)
Optically pure (R,Z)-5-dec-1-enyloxacyclopentan-2-one (1) has been synthesised from methyl 4-oxotetradec-5-ynoate (2) by chiral reduction with 9-(pinan-3-yl)-9-borabicyclononane (3) which yielded the R-alcohol (4), in 74percent enantiomeric excess.This was further purified by recrystallisation of the salt formed from the phthalate ester of compound (4) and (+)-α-methylbenzylamine and then hydrolysed and converted into (R,Z)-(-)-(1).
