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5-Substituted Derivatives of the Tricyclic (+)-Sparteine Surrogate in the Enantioselective Lithiation/Stannylation of anO-Alkyl Carbamate

Title data

Breuning, Matthias ; Hein, David:
5-Substituted Derivatives of the Tricyclic (+)-Sparteine Surrogate in the Enantioselective Lithiation/Stannylation of anO-Alkyl Carbamate.
In: European Journal of Organic Chemistry. (2013) Issue 33 . - pp. 7575-7582.
ISSN 1099-0690
DOI: https://doi.org/10.1002/ejoc.201300987

Abstract in another language

5-Mono- and 5,5-disubstituted tricyclic bispidines, derivatives of the known (+)-sparteine surrogate, have been synthesized in four-to-six steps from the natural alkaloid (–)-cytisine and evaluated as chiral ligands in the enantioselective lithiation/stannylation of an O-alkyl carbamate. Structure–selectivity studies revealed that a small 5-endo substituent is tolerated, whereas larger 5-endo substituents and even small 5-exo substituents lead to significantly reduced levels of chirality transfer.

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: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 13:09
Last Modified: 11 Jan 2022 13:09
URI: https://eref.uni-bayreuth.de/id/eprint/68304