Journal article
Regioselectivity in the syntheses of Enantiopure 2-Benzopyrans through Intramolecular cyclization of tethered Lactaldehydes. Conformations of the products
Australian Journal of Chemistry, Vol.56(5), pp.489-498
2003
Abstract
Using titanium tetraisopropoxide, the enantiopure tethered lactaldehyde (α′ S,2S)-2-(3′-hydroxy-α′-methyl-benzyloxy)propanal (6) is cyclized with complete regio- and diastereoselectivity ortho to the phenolic hydroxyl group to give (1S,3S,4R)-3,4-dihydro-1,3-dimethyl-2-benzopyran-4,5-diol (7). Similar cyclization of the epimeric (α′ R,2S)-lactaldehyde (25) yields solely the corresponding (1R,3S,4R)-4,5-diol (34). The 4,5-diacetate (26), but not (35), undergoes conformational inversion of the heterocyclic ring through significant 4,5-peri interactions between the adjacent acetoxy substituents. Spontaneous cyclizations of the corresponding phenoxide ions of the lactalde-hydes (6) and (25), generated by fluoride from their silyl ethers, led to the related 4,7-diols with high regioselectivity through ring-closure para to the aromatic oxygen.
Details
- Title
- Regioselectivity in the syntheses of Enantiopure 2-Benzopyrans through Intramolecular cyclization of tethered Lactaldehydes. Conformations of the products
- Authors/Creators
- R. Aggarwal (Author/Creator)A.A. Birkbeck (Author/Creator)R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)Y. Gruchlik (Author/Creator)F.J. Oosthuizen (Author/Creator)
- Publication Details
- Australian Journal of Chemistry, Vol.56(5), pp.489-498
- Publisher
- Commonwealth Scientific and Industrial Research Organization Publishing
- Identifiers
- 991005540439507891
- Copyright
- © 2003 CSIRO
- Murdoch Affiliation
- School of Chemical and Mathematical Science
- Language
- English
- Resource Type
- Journal article
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