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Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra-hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization
- Issue Date
- Oct-2013
- Publisher
- Georg Thieme Verlag
- Keywords
- cyclization; Lewis acids; oxonium ion; diastereoselectivity; 2; 4; 6-trisubstituted tetrahydropyrans
- Citation
- Synlett, v.24, no.17, pp 2292 - 2296
- Pages
- 5
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- Synlett
- Volume
- 24
- Number
- 17
- Start Page
- 2292
- End Page
- 2296
- ISSN
- 0936-5214
1437-2096
- Abstract
- We have described a highly diastereoselective synthesis of 2,6-disubstituted 4-(dimethoxymethyl)tetrahydropyrans via TMSOTf-promoted Prins-pinacol reaction of methylene diol with acetals. This reaction provides an efficient procedure to synthesize functionalized tetrahydropyrans containing an acetal group at the C4 position with all-cis 2,4,6 relative configuration.
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Related Researcher
- Min, Sun Joon
- COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY (DEPARTMENT OF CHEMICAL AND MOLECULAR ENGINEERING)