THE REDUCTION OF ALDEHYDES AND KETONES
The reduction of (5)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene was optimized for diastereoselectivity and overall conversion to (2,3,5)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane (2a). A two-step reduction sequence is described wherein the enamine is reduced with a borane-sulfonate derivative followed by reduction of the resulting ketone with sodium borohydride. The desired 2a was obtained with 84% diastereoselectivity and an acyclic 1,4 stereoinduction ratio of 14:1. This methodology has been used to produce multikilogram quantities of the diamino alcohol core of Ritonavir and should be general to the synthesis of related diamino hydroxyethylene isosteres.
Health Effects of Alcohol and Aldehyde Oxidations:
In general terms, reduction of an aldehyde leads to a .
When a person ingests alcohol, the reactions listed below occur in the liver with the aid of enzymes. The accumulation of acetaldehyde may produce nausea. Eventually, the acetaldehyde is converted to acetic acid which can be further metabolized without any problem.
Reduction of a ketone leads to a .
This page looks at the reduction of aldehydes and ketones by two similar reducing agents - lithium tetrahydridoaluminate(III) (also known as lithium aluminium hydride) and sodium tetrahydridoborate(III) (sodium borohydride).