Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A
1996; Elsevier BV; Volume: 37; Issue: 49 Linguagem: Inglês
10.1016/s0040-4039(96)02055-2
ISSN1873-3581
AutoresÁngel González, Josep Aiguadé, Fèlix Urpı́, Jaume Vilarrasa,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAsymmetric 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; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield.
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