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The dianion of β-keto esters are alkylated at the γ-carbon with 3-bromo-1-trimethyIsilyl-1-propyne. The resulting alkynes are hydrated (H 3 O + , Hg 2+ ) 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.

canadian journal of chemistry

Utilization of trimethylsilylpropyne as an acetonyl unit in the synthesis of cyclopentenones. Applications to the synthesis of jasmone and dihydrojasmone