Inositols as chiral templates: 1,4-conjugate addition to tethered cinnamic esters.
The 1,4-addition of thio nucleophiles to chiro-inositols containing a cinnamyl Michael acceptor proceeded with excellent diastereochemical induction and good yields. Cleavage of the inositol auxiliary provides beta-thio hydrocinnamic acids in >99% ee's.
Cousins
Ghislaine
G
School of Chemical and Physical Sciences, Victoria University of Wellington, New Zealand.
Falshaw
Andrew
A
Hoberg
John O
JO
D002934:Cinnamates / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006868:Hydrolysis; D007294:Inositol / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002934:Cinnamates; D004952:Esters; D007294:Inositol; D003300:Copper