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Enantioselective borane reduction of ketones catalyzed by tricyclic 1,3,2-oxazaborolidines

Title data

Kaldun, Johannes ; Krimalowski, Alexander ; Breuning, Matthias:
Enantioselective borane reduction of ketones catalyzed by tricyclic 1,3,2-oxazaborolidines.
In: Tetrahedron Letters. Vol. 57 (2016) Issue 23 . - pp. 2492-2495.
ISSN 0040-4039
DOI: https://doi.org/10.1016/j.tetlet.2016.04.091

Abstract in another language

Two novel tricyclic 1,3,2-oxazaborolidines were synthesized in seven steps from methyl Boc-l-pyroglutamate. They are characterized by an ortho- and peri-fused 5/5/6-ring system with the B–N bond forming one ring junction. In the asymmetric borane reduction of ketones, the B-alkoxy bridged derivative permits excellent enantioselectivities of up to 98% ee and its activity is comparable to that of the standard CBS catalyst. The closely related, B-alkyl bridged derivative is less enantioselective and less active, as determined by competition experiments.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: CBS reduction; Oxazaborolidine; Enantioselective catalysis; Pyrrolidine; Amino diol
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 10:01
Last Modified: 11 Jan 2022 10:01
URI: https://eref.uni-bayreuth.de/id/eprint/68299