Camphor-derived chiral boryl enolates are highly reactive and
highly anti-stereoselective enolate
synthon systems in aldol addition reactions promoted by a
TiCl4 or SnCl4 cocatalyst.
More
significantly, this high-yield reaction exhibits remarkable generality
with respect to the aldehyde
nature, as illustrated by the rapid and anti-stereoselective
aldolizations with the simple saturated
and unsaturated aliphatic aldehydes, and aromatic aldehydes at
temperatures as low as −90 °C.
The enhanced reaction generality and anti stereoselectivity of
camphor-derived boryl enolates
suggests the importance of the nature of chiral auxiliary architecture
in determining the aldol
bond construction process. Final nondestructive camphor-based
auxiliary removal via hydroperoxide-mediated hydrolysis affords enantiomerically pure
anti-β-hydroxy-α-methyl aldol products.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.