Abstract
Organocopper reagents associated with a strong Lewis acid such as BF 3 react with the C— O single bond of orthoesters, acetals and epoxides. The diastereoselective cleavage of chiral acetals opens a new way of obtaining chiral secondary alcohols or chiral (3-substituted aldehydes. A partial synthesis of the pherom one of the California red scale uses this approach. The opening of hindered epoxides is also very efficient with R 2 CuLi/BF 3 reagents. Thus reaction with epoxy-silane gives rise to conjugated dienes as illustrated with the synthesis of the pheromones of Lobesia botrana and of Bombyx mori. Cyclohexene oxide reacts in the same way with R 4 AlLi/BF 3 and the dienyl substituted cyclohexanols, thus obtained, can be used in highly stereoselective intram olecular Diels-Alder reactions.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Philosophical Transactions of the Royal Society of London. Series A, Mathematical and Physical Sciences
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
