Prediction and experimental verification of the stereoselective electrocyclization of 3-formylcyclobutene
K Rudolf, DC Spellmeyer, KN Houk
Index: Rudolf, Klaus; Spellmeyer, David C.; Houk, K. N. Journal of Organic Chemistry, 1987 , vol. 52, # 16 p. 3708 - 3710
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Citation Number: 82
Abstract
The coupling of the two optically active subunits 13 and 8a-c20 required a chelation-controlled aldol reaction2' to achieve high levels of stereochemical efficiency. Although the reactions between the trimethylsilyl enol ether derived from the methyl ketone 13 and the protected aldehydes 8a-c in the presence of SnCl, (CH,Cl,, -78 - -20 "C) provided mixtures of the adducts 14 and 15 in which the desired diastereoisomer 14 dominated by as much as 9:1, the yields ...
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