Utilization of trimethylsilylpropyne as an acetonyl unit in the synthesis of cyclopentenones. Applications to the synthesis of jasmone and dihydrojasmone
- 1 September 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (17) , 2301-2304
- https://doi.org/10.1139/v78-379
Abstract
The dianion of β-keto esters are alkylated at the γ-carbon with 3-bromo-1-trimethyIsilyl-1-propyne. The resulting alkynes are hydrated (H3O+, Hg2+) and cyclized (OH−) to the corresponding cyclopentenones, jasmone and dihydrojasmone. The failure to obtain cyclopentanones from the acid- and base-catalyzed cyclizations of 6-substituted 3-keto esters may be rationalized by Baldwin's rules for cyclization.This publication has 0 references indexed in Scilit: