Tetrahedron

Stereoselective alkenylation of aldehydes with phosphorus carbanions: Preparation of E-and Z-2-alkoxy-and 2-aryloxy-2-alkenoates

P Seneci, I Leger, M Souchet, G Nadler

Index: Seneci, Pierfausto; Leger, Isabelle; Souchet, Michel; Nadler, Guy Tetrahedron, 1997 , vol. 53, # 50 p. 17097 - 17114

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Citation Number: 19

Abstract

Eighteen phosphorus-based alkenylation reagents 1a–6c were synthesized and condensed with n-butyraldehyde 7a and benzaldehyde 7f. They were condensed with the aldehydes 7b- e, gn to produce 2-methoxy-2-alkenoates 8a-n and 2-phenoxy-2-alkenoates 9a-n. A discussion on different selectivities for the alkenylation reagents under different experimental conditions (base, solvent, temperature), the influence of the aldehydes on ...