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Asymmetric nucleophilic addition to β- and γ-alkoxy aldehydes using carbohydrate as a chiral auxiliary

✍ Scribed by Tomoyasu Yoshida; Jun-ichi Chika; Hisashi Takei

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 243 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00717-5

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✦ Synopsis

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).

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