A synthesis of enantiomerically enriched propargyl silanes

I Fleming, JM Mwaniki

Index: Fleming, Ian; Mwaniki, Joseph M. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 7 p. 1237 - 1247

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Citation Number: 14

Abstract

Reduction of ethyl 3-methyl-, 3-isopropyl-and 3-n-pentyl-3-[dimethyl (phenyl) silyl] propanoates 4 with DIBAL to the aldehydes 5, enol trifluoromethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2, 6-di-tert-butylpyridine, and elimination using LDA, gives the propargyl silanes 8. The esters 4 could also be prepared enantiomerically enriched (11), and the final products are the enantiomerically enriched ...