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Enantioselective synthesis of sec-allylalcohols by catalytic asymmetric addition of divinylzinc to aldehydes.

✍ Scribed by Wolfgang Oppolzer; Rumen N. Radinov

Book ID
104216846
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
280 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Readily available chiral tridentate ligand & catalyzes the highly Si-face selective addition of diethyl-, di-n-propylzinc and, more significantly, of divinylzinc to aromatic and aliphatic aldehydes whereas bidentate ligands 11 and u exert a topologically reversed catalytic bias.

Asymmetric formation of C,C-bonds by means of chiral catalysts is a formidable challenge to the organic chemist '). Recent years have witnessed very encouraging progress on Baminoalcohol catalyzed x-face selective 1,2-additions of diethylzinc to aldehydes (1 + 2 + 3 or 4, Scheme 1) 2B3).

πŸ“œ SIMILAR VOLUMES

Enantioselective addition of (Z)- and (E
Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols
✍ Wolfgang Oppolzer; Rumen N. Radinov πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 French βš– 249 KB

In situ prepared (Z)-and (E)-1 -alkenylzinc bromides 5 were added to various aldehydes 1 in the presence of lithiated (+)-N-methylephedrine or (+)-2-(NJ-dimethylamino)-1,2\_diphenylethanol to give sec. allylalcohols 7 in high optical purity with simple recovery of the chiral amino1 6. Asymmetric lig