Diastereoselective Construction of alpha-Silyltetrahydropyranols through Silyl-Oxa-Prins Cyclization
The Bronsted acid mediated selective silyl-oxa-Prins cyclization of alpha-silyloxy homoallylsilanes with various aldehydes was achieved. Synthetically valuable alpha-silyltetrahydropyranol products were obtained in high yields with excellent diastereo-selectivities. Both syn- and anti-isomeric tetrahydropyranols were selectively obtained by tuning the olefinic geometry of the substrates. The procedure is operationally simple and convenient to perform even on a large scale under mild conditions.
- Publisher
- WILEY-V C H VERLAG GMBH
- Issue Date
- 2017-01
- Language
- English
- Article Type
- Article
- Keywords
LADDER POLYETHER SYNTHESIS; NATURAL-PRODUCT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; BRONSTED ACIDS; 2,3,4,6-TETRASUBSTITUTED TETRAHYDROPYRANS; HOMOALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; ALKYL TOSYLATES; DELTA-LACTONES; ALDEHYDES
- Citation
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2017, no.4, pp.933 - 938
- ISSN
- 1434-193X
- Appears in Collection
- CH-Journal Papers(저널논문)
- Files in This Item
- There are no files associated with this item.
This item is cited by other documents in WoS
| ⊙ Detail Information in WoSⓡ | Click to see |  |
| ⊙ Cited 1 items in WoS | Click to see citing articles in |  |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.