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Title

Boron fluoride promoted cleavage of acetals by organocopper reagents. Application to asymmetric synthesis

Authors
Normant, Jean F.
Ghribi, A.
Mangeney, Pierre
Published in Tetrahedron. 1989, vol. 45, no. 2, p. 507-516
Abstract In the presence of BF3. Et2O, organocopper and cuprate reagents promote the substitution of one alkoxy group of an acetal. Under the same conditions, alkoxy tetrahydropyrans react selectively, by ring cleavage. Chiral cyclic acetals, having a C2 axis of symmetry are diastereoselectively cleaved. The method serves to synthesize chiral secondary alcohols, after the removal of the chiral auxiliary.
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NORMANT, Jean F. et al. Boron fluoride promoted cleavage of acetals by organocopper reagents. Application to asymmetric synthesis. In: Tetrahedron, 1989, vol. 45, n° 2, p. 507-516. https://archive-ouverte.unige.ch/unige:8174

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