Tetrahedron

Alkynenitriles: stereoselective chelation controlled conjugate addition–alkylations

FF Fleming, V Gudipati, OW Steward

Index: Fleming, Fraser F.; Gudipati, Venugopal; Steward, Omar W. Tetrahedron, 2003 , vol. 59, # 29 p. 5585 - 5593

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Citation Number: 21

Abstract

Chelation-controlled conjugate addition of Grignard reagents to γ-hydroxyalkynenitriles stereoselectively generates tri-and tetra-substituted alkenenitriles. t-BuMgCl-initiated deprotonation of hydroxyalkynenitriles followed by addition of a second Grignard reagents triggers a facile conjugate addition leading to a cyclic magnesium chelate. Protonation of the chelate stereoselectively generates trisubstituted nitriles whereas the addition of t-BuLi ...