Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon

SA Shaw, P Aleman, J Christy, JW Kampf…

Index: Shaw, Scott A.; Aleman, Pedro; Christy, Justin; Kampf, Jeff W.; Va, Porino; Vedejs, Edwin Journal of the American Chemical Society, 2006 , vol. 128, # 3 p. 925 - 934

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Citation Number: 172

Abstract

The chiral, nucleophilic catalyst TADMAP [1, 3-(2, 2, 2-triphenyl-1-acetoxyethyl)-4- (dimethylamino) pyridine] has been prepared from 3-lithio-4-(dimethylamino) pyridine (5) and triphenylacetaldehyde (3), followed by acylation and resolution. TADMAP catalyzes the carboxyl migration of oxazolyl, furanyl, and benzofuranyl enol carbonates with good to excellent levels of enantioselection. The oxazole reactions are especially efficient and are ...

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