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Reaction of chiral titanium Z-enolates with chiral α-silyloxy aldehydes. Syntheses of NFX-2 and Antimycinone

✍ Scribed by Cristina Esteve; Mònica Ferreró; Pedro Romea; Fèlix Urpí; Jaume Vilarrasa

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
180 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Titanium-mediated aldol reactions of 1 and (S)-2-tert-butyldiphenylsilyloxy aldehydes ( matched pair) afford syn Felkin diastereomers in excellent yield and absolute stercochemical control. Having established that chain length does not affect the yield of the titanium aldol reactions, we have been able to achieve short, high yielding and enantioselective syntheses of NFX-2 and Antimycinone.

📜 SIMILAR VOLUMES

Reaction of achiral titanium Z-enolates
Reaction of achiral titanium Z-enolates with chiral α-silyloxy aldehydes
✍ Cristina Esteve; Mònica Ferreró; Pedro Romea; Fèlix Urpí; Jaume Vilarrasa 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 184 KB

Aldol reactions between the putative Z-enolate derived from 2-methyl-3-pentanone and several chiral ot-tert-butyldiphcnylsilyioxy aldehydes have been studied. The stereoehemical outcome suggests that stereoelectronic effects play a dominant role in these reactions and the results can be accommodated