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Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0²,⁷]tridecane

Title data

Breuning, Matthias ; Steiner, Melanie:
Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0²,⁷]tridecane.
In: Tetrahedron: Asymmetry. Vol. 19 (2008) Issue 16 . - pp. 1978-1983.
ISSN 0957-4166
DOI: https://doi.org/10.1016/j.tetasy.2008.08.002

Abstract in another language

The enantiomerically pure tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 14:19
Last Modified: 11 Jan 2022 14:19
URI: https://eref.uni-bayreuth.de/id/eprint/68315