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

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Abstract

Readily available chiral tridentate ligand 8 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 12 exert a topologically reversed catalytic bias.

Ligand 8 (2 mol%) catalyzes the addition of divinylzinc to aromatic and aliphatic aldehydes 1 giving allylalcohols 3 in 82 to 88% e.e. (with 20 mol% of 8: ~100% e.e.)

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