Enantioselective ring cleavage of dioxane acetals mediated by a chiral Lewis acid: Application to asymmetric desymmetrization of meso-1,3-diols

Authors
Harada, T Sekiguchi, K Nakamura, T Suzuki, J Oku, A
Citation
T. Harada et al., Enantioselective ring cleavage of dioxane acetals mediated by a chiral Lewis acid: Application to asymmetric desymmetrization of meso-1,3-diols, ORG LETT, 3(21), 2001, pp. 3309-3312
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
21
Year of publication
2001
Pages
3309 - 3312
Database
ISI
SICI code
1523-7060(20011018)3:21<3309:ERCODA>2.0.ZU;2-M
Abstract
[GRAPHICS] Phenylalanine-derived B-aryl-N-tosyloxazaborolidinones selectively activate one of two enantiotopic oxygen atoms in prochiral anti dioxane acetals der ived from meso-1,3-diols, leading to enantioselective formation of ring-cle avage products. The reaction is utilized as a key step in asymmetric desymm etrization of meso-1,3-diols.