Canadian journal of chemistry

Folding strain stereocontrol in cyclohexane ring formation by means of an intramolecular ester enolate alkylation reaction

T Tokoroyama, H Kusaka

Index: Tokoroyama, Takashi; Kusaka, Hisashi Canadian Journal of Chemistry, 1996 , vol. 74, # 12 p. 2487 - 2502

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Citation Number: 13

Abstract

Diastereoselectivity in the cyclization of ethyl 7-bromo-2-methylheptanoates with an additional substituent at various positions in the chain, by LDA treatment, was investigated in connection with the concept of folding strain stereocontrol. Cyclization of 3-, 4-, and 6-methyl- substituted substrates revealed high selectivity, which demonstrates the prevalence of folding strain stereocontrol and the usefulness of this approach for stereoselective ring ...