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

DOI: 10.1016/S0040-4039(98)00717-5

Source and publish data:

Tetrahedron Letters p. 4305 - 4308 (1998)

Update date:2022-08-04

Topics:

Authors:

Yoshida, Tomoyasu

Chika, Jun-Ichi

Takei, Hisashi

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Article abstract of DOI:10.1016/S0040-4039(98)00717-5

The nucleophilic addition of Grignard reagents and allyltributyltin to chiral ω-tetrahydropyranloxy propanal and butanal derived from L-fucose and D-arabinose gave the alcohols with high diastereoselectivity (up to 51% de by 1,6-asymmetric induction and 95% de by 1.5-asymmetric induction).

Full text of DOI:10.1016/S0040-4039(98)00717-5

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