Dettierastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetrahydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization
- Dettierastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetrahydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization
- 김영습; 이재균; 배애님; 조용서; 민선준
- cyclization; Lewis acids; oxonium ion; diastereoselectivity; 2,4,6-trisubstituted tetrahydropyrans
- Issue Date
- VOL 24, NO 17, 2292-2296
- 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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