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Asymmetric allylation of aldehydes using tiglyltitanocenes attached to a carbohydrate

✍ Scribed by Didier Felix; Jan Szymoniak; Claude Moïse

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
640 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

rl3-Tiglyltitanium complexes bearing ct-or [~-glucopyranosyl auxiliaries were synthesized starting from the corresponding Cl-dienopyranosides. These complexes were reacted with propanal and (-)-myrtenal to afford 4-hydroxy-3methylvinylglycoside derivatives. In several cases, high diastereofaciat selectivities were obtained. Thus, the reaction employing (-)-myrtenal and [~-glucopyranosyl tiglyltitanium complex led to the unique (d.s._>98%) 3R,4R-configurated compound bearing the sugar and pinenyl fragments, which can be considered as a promising new chiron.

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Asymmetric nucleophilic addition to β- a
Asymmetric nucleophilic addition to β- and γ-alkoxy aldehydes using carbohydrate as a chiral auxiliary
✍ Tomoyasu Yoshida; Jun-ichi Chika; Hisashi Takei 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 243 KB

The nucleophilic ad~tion of Grignard reagents and allyltributyltin to chiral c0-tetrahyckopynmyioxy propanal and butanal drayed from L-fucose and D-arabinose gave the corresponding alcohols with high diastereoselectivity (up to 51% de by 1,6-asymmelric induction and 95% de by 1,5asymmetric induction