Atroposelectivity in the electrophilic substitution reactions of laterally lithiated and silylated tertiary amides

…, JH Pink, N Westlund, CS Frampton

Index: Clayden, Jonathan; Pink, Jennifer H.; Westlund, Neil; Frampton, Christopher S. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 7 p. 901 - 917

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Citation Number: 24

Abstract

Lateral lithiation–electrophilic quench of 2-alkyl-1-naphthamides and 2, 6- dialkylbenzamides yields products containing an atropisomeric Ar–CO axis and a new stereogenic centre with high (generally> 95∶ 5) diastereoselectivity. With imines as electrophiles, single diastereoisomers containing an atropisomeric axis and two new stereogenic centres are formed. 2, 6-Dialkylbenzamides may be functionalised ...