Tetrahedron letters

Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

Á González, J Aiguadé, F Urpí, J Vilarrasa

Index: Gonzalez, Angel; Aiguade, Josep; Urpi, Felix; Vilarrasa, Jaume Tetrahedron Letters, 1996 , vol. 37, # 49 p. 8949 - 8952

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Citation Number: 83

Abstract

Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione- derived enolates,(ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2, 2′-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; eg, C5-C12 fragment 7 has been isolated ...