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Indium-mediated diastereoselective allylation reactions: preparation of tert-α-hydroxy acids

✍ Scribed by Jeong Ah Shin; Joo Hwan Cha; Ae Nim Pae; Kyung Il Choi; Hun Yeong Koh; Han-Young Kang; Yong Seo Cho

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
202 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Indium-mediated allylation reactions of a-ketoimides derived from Oppolzer's sultam were accomplished in aqueous THF in good yields and excellent diastereomeric excesses. It could be a useful method for the preparation of enantiopure t-a-hydroxy acids. When the substituent of a-ketoimides was changed from phenyl to thiophenyl or furyl group, diastereoselectivity decreased in comparison to N-phenyl derivatives, but changing solvent to aqueous ethanol provided improved levels of diastereoselectivity.

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✍ Teck-Peng Loh; Kui-Thong Tan; Jian-Ying Yang; Chao-Li Xiang 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 56 KB

Linear a homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic in origin from the results presented in this p