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Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.
- Source :
-
Organic letters [Org Lett] 2009 Sep 03; Vol. 11 (17), pp. 3958-61. - Publication Year :
- 2009
-
Abstract
- Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl(4) produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon nucleophiles.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 11
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 19663466
- Full Text :
- https://doi.org/10.1021/ol901613k