77981-87-4

Upstream product

• 95061-49-7 3-Hydroxy-4-methyl-pentanoic acid (R)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 87319-84-4 (1'R,3R)-3-Hydroxy-N-(2-hydroxy-1-phenylethyl)-4-methylpentanamid 
• 204577-77-5 (R)-3-Hydroxy-1-((1R,2R,4R)-2-hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-4-methyl-pentan-1-one 

Relevant academic research and scientific papers

Highly diastereoselective aldol reactions with camphor-based acetate enolate equivalents

New lithium enolates of α-hydroxy ketones, derived from camphor, are evaluated for asymmetric aldol reactions in the presence of lithium chloride. The diastereoselectivity of the reactions between the lithium enolate of 3 and a variety of achiral aldehydes is strongly influenced by the lithium chloride salt. In these instances, the achieved levels of asymmetric induction, typically 95:5 dr, are in the range of those attained in aldol reactions involving the lithium enolate of the methyl ketone 4, which is sterically more demanding. The resulting aldol adducts are easily transformed into β-hydroxy carboxylic acids, ketones, and aldehydes with concomitant recovery of the camphor, the chiral controller of the process, which can be reused.

(R)- AND (S)-2-ACETOXY-1,1,2-TRIPHENYLETHANOL - EFFECTIVE SYNTHETIC EQUIVALENTS OF A CHIRAL ACETATE ENOLATE

The enolate 3, easily available by double deprotonation of (R)-2-acetoxy-1,1,2-triphenylethanol (5), adds in a highly stereoselective manner to aldehides.Hydrolysis of the adducts 6/7 affods the acids 2.