The Asymmetric Synthesis Of β-Hydroxy Ketone And Chiral α-Amino Acid From Natural Camphor

The dissertation studies the applications of natural camphor in asymmetric synthesis andβ-hydroxy ketones drivied from camphor were synthetied which were applicati-ed in synthesis of threeα-Amino acids.The dissertation consisted of three parts:(1)Study on the synthesis of sily enol ether of camphor:Two sily enol ethers of camphor were synthesized with 96.3%,90%of totla yield by camphor reacting with trimethylchlorosilane and tert-Butyldimethylsilyl chloride in THF and LDA at -78℃. (2)Five chrialβ-hydroxys were synthesized successfully with excellent chemical yield(87%～96%)and high diastereomeric excesses(d.e.96%～99%)using different aldehydes in Mukaiyama Adol reaction.(3)Preliminary test of the asymmetric synthesis of a-Amino acid:A series of new schiff base,yield 5%～55%,were first preparied from p-hydroxy ketone(3a,3e)drivied from camphor and glycine ester. Under optimizing the alkylation of 6b₁,6b₂ and hydrolysis of 8a₂～8c₂,three amino acids were synthesized.The best enantionmeric excesses(e.e.98%)of L-Phenylalanine was synthesized from 6b₂ and benzyl bromo by comparing the alkylation of 6b₁ with 6b₂ and hydrolyzing 8a₂～8c₂.