Huy, Peter H., Westphal, Julia C. and Koskinen, Ari M. P. (2014). Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxy-piperidines - development of a phosphite-driven cyclodehydration. Beilstein J. Org. Chem., 10. S. 369 - 384. FRANKFURT AM MAIN: BEILSTEIN-INSTITUT. ISSN 1860-5397
Full text not available from this repository.Abstract
A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.
Item Type: | Journal Article | ||||||||||||||||
Creators: |
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URN: | urn:nbn:de:hbz:38-445934 | ||||||||||||||||
DOI: | 10.3762/bjoc.10.35 | ||||||||||||||||
Journal or Publication Title: | Beilstein J. Org. Chem. | ||||||||||||||||
Volume: | 10 | ||||||||||||||||
Page Range: | S. 369 - 384 | ||||||||||||||||
Date: | 2014 | ||||||||||||||||
Publisher: | BEILSTEIN-INSTITUT | ||||||||||||||||
Place of Publication: | FRANKFURT AM MAIN | ||||||||||||||||
ISSN: | 1860-5397 | ||||||||||||||||
Language: | English | ||||||||||||||||
Faculty: | Unspecified | ||||||||||||||||
Divisions: | Unspecified | ||||||||||||||||
Subjects: | no entry | ||||||||||||||||
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URI: | http://kups.ub.uni-koeln.de/id/eprint/44593 |
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