Title

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

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Apr 20th, 9:00 AM Apr 20th, 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.