Journal of the American Chemical Society

Aldol additions of pinacolone lithium enolate with ketones: reactivities governed predominantly by field effects

G Das, ER Thornton

Index: Das, Goutam; Thornton, Edward R. Journal of the American Chemical Society, 1993 , vol. 115, # 4 p. 1302 - 1312

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Citation Number: 27

Abstract

Abstract: The relative reactivities of representative a-and 8-heterosubstituted acyclic, cyclic (five-and six-membered), and aromatic ketones with the lithium enolate of pinacolone in diethyl ether at-78 OC were determined. The order of reactivities of monosubstituted acetones (MeCOCH2X) is X= C1> OTBDMS> OMe> SMe> NMe2> CH2SMe> H> Me and spans a range of lo4. Excellent correlation was obtained for MeCOCH, X when log (kx/ ...

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