Synthesis of 1-t-Butyl-2-phenyl-3-(trimethylsiyl)-3-cyanocyclopropene

CHED 882

Rachael A Vaubel, Department of Chemistry, Luther College, 700 College Drive, Decorah, IA 52101 and Steven R. Kass, Department of Chemistry, University of Minnesota, 207 Pleasant St. S.E, Minneapolis, MN 55455.
A racemic mixture of alcohol 1 was prepared in five steps starting from phenylacetylene and ethyl diazoacetate. This alcohol was then reacted with a (S)-(+)-mandelic acid derivative to produce a mixture of diastereomers 2. Next, these diastereomers will be separated either by crystallization or MPLC. Ester 2 will be converted to nitrile 3 in three steps. The absolute configuration of starting materials and products must be established. Then, kinetic experiments to determine the inversion barrier of its cyclopropenyl anion will be carried out.

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