Abstract
Canales and Corey report a remarkably short and efficient synthesis of estrone methyl ether which exploits a novel N-methyloxazaborolidinium cation as a Lewis acid catalyst for an asymmetric Diels-Alder reaction. The paper cites ten further examples all proceeding with excellent yields and ee values. The reactions typically proceed in dichloromethane at -78 ˚C but in the estrone synthesis depicted, the cycloaddition was performed at room temperature. The ee of the adduct D (82%) was raised to 99% by one recrystallization.
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