Stereoselectivity in the reaction of iodonium ion with dihydropyran
Poster Number
26
Format
Poster Presentation
Abstract/Artist Statement
In order to study the stereoselective halogenation reaction of dihydropyran with halonium electrophiles, gas phase ab initio calculations have been performed on the chiral bridged intermediate. The effect of different a-substituted alkane groups are studied in order to determine relative stabilities of the syn- and anti- isomers of the intermediate, which break up to form the S,S- and R,R- enantiomers, respectively. The effect on the stereoselectivity of the final products is described, supporting experimental results. While little sensitivity to substituent group is found, a-substitution in general is found to stabilize the syn- intermediate relative to the anti- form.
Location
Pacific Geosciences Center
Start Date
20-4-2002 9:00 AM
End Date
20-4-2002 5:00 PM
Stereoselectivity in the reaction of iodonium ion with dihydropyran
Pacific Geosciences Center
In order to study the stereoselective halogenation reaction of dihydropyran with halonium electrophiles, gas phase ab initio calculations have been performed on the chiral bridged intermediate. The effect of different a-substituted alkane groups are studied in order to determine relative stabilities of the syn- and anti- isomers of the intermediate, which break up to form the S,S- and R,R- enantiomers, respectively. The effect on the stereoselectivity of the final products is described, supporting experimental results. While little sensitivity to substituent group is found, a-substitution in general is found to stabilize the syn- intermediate relative to the anti- form.