Palladium-and Copper-Catalyzed 1, 4-Additions of Organozinc Compounds to Conjugated Aldehydes

JA Marshall, M Herold, HS Eidam, P Eidam

Index: Marshall, James A.; Herold, Martin; Eidam, Hilary S.; Eidam, Patrick Organic Letters, 2006 , vol. 8, # 24 p. 5505 - 5508

Full Text: HTML

Citation Number: 22

Abstract

In the course of recent studies on additions of allenylzinc reagents, prepared from propargylic mesylates as described above, to conjugated aldehydes, we encountered an unforeseen side reaction in which an ethyl group from the diethylzinc was transferred to the β-position of (E)-2-heptenal in a 1,4-addition reaction (Figure 2). 2 In a separate experiment, we found that the 1,4-ethyl adduct was produced in high yield from the enal and diethylzinc in the ...