Highly Diastereoselective Conjugate Addition of Lithiated γ-Crotonolactone (But-2-en-4-olide) to Cyclic Enones To Give Syn-Adducts: Application to a Brefeldin …

…, SC Vonwiller, TW Hambley, P Lelandais

Index: Haynes, Richard K.; Lam, William W.-L.; Yeung, Lam-Lung; Williams, Ian D.; Ridley, Andrew C.; Starling, Scott M.; Vonwiller, Simone C.; Hambley, Trevor W.; Lelandais, Patrick Journal of Organic Chemistry, 1997 , vol. 62, # 14 p. 4552 - 4553

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Citation Number: 23

Abstract

Lithiated allylic sulfoxides and phosphine oxides undergo diastereoselective conjugate addition to cyclic enones to provide vinylic products whose stereochemistry concisely relates to the geometry of the double bond in the starting allylic system. 1 From (E)-allylic systems are obtained syn-, and from (Z), the anti-, products. 1 There is substantial impetus for application of the process to carbonyl-stabilized allylic systems, 2 in particular those ...