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

Normant, Jean F.; Alexakis, Alexandre; Ghribi, A.; Mangeney, Pierre

doi:10.1016/0040-4020(89)80078-X

Scientific article

English

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

ContributorsNormant, Jean F.; Alexakis, Alexandre; Ghribi, A.; Mangeney, Pierre

Published inTetrahedron, vol. 45, no. 2, p. 507-516

Publication date1989

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.

Affiliation Not a UNIGE publication

Citation (ISO format)

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. doi: 10.1016/0040-4020(89)80078-X

Article (Published version)

Identifiers

PID : unige:8174
DOI : 10.1016/0040-4020(89)80078-X

ISSN of the journal0040-4020

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

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