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Chiral 2-endo-Substituted 9-Oxabispidines : Novel Ligands for Enantioselective Copper(II)-Catalyzed Henry Reactions

Title data

Breuning, Matthias ; Hein, David ; Steiner, Melanie ; Gessner, Viktoria H. ; Strohmann, Carsten:
Chiral 2-endo-Substituted 9-Oxabispidines : Novel Ligands for Enantioselective Copper(II)-Catalyzed Henry Reactions.
In: Chemistry : a European Journal. Vol. 15 (2009) Issue 46 . - pp. 12764-12769.
ISSN 1521-3765
DOI: https://doi.org/10.1002/chem.200901789

Abstract in another language

A flexible approach, applicable on a gram scale, to chiral 2-endo-substituted 9-oxabispidines was developed. The key intermediate, a cis-configured 6-aminomethylmorpholine-2-carbonitrile, was prepared from (R)-3-aminopropane-1,2-diol and 2-chloroacrylonitrile. The 2-endo substituent was introduced by Grignard addition, cyclization, and exo-selective reduction, thus furnishing the enantiomerically pure bi- and tricyclic 9-oxabispidines in 19–59 % yield. The CuCl2 complex of the tricyclic 9-oxabispidine, which carries an 2-endo,N-anellated piperidine ring, is an excellent catalyst for enantioselective Henry reactions giving the S-configured β-nitro alcohols in 91–98 % ee (13 examples). Surprisingly, the analogous copper complexes of the bicyclic 9-oxabispidines delivered the enantiocomplementary R-configured products in 33–57 % ee. The respective transition states were discussed.

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 14:05
Last Modified: 11 Jan 2022 14:05
URI: https://eref.uni-bayreuth.de/id/eprint/68312