Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Huy, Peter H. UNSPECIFIED UNSPECIFIED UNSPECIFIED Westphal, Julia C. UNSPECIFIED UNSPECIFIED UNSPECIFIED Koskinen, Ari M. P. UNSPECIFIED UNSPECIFIED UNSPECIFIED
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
Uncontrolled Keywords:	Keywords Language ASYMMETRIC-SYNTHESIS; SUBSTANCE-P; AMINO-ACIDS; LITHIUM TRIETHYLBOROHYDRIDE; EXCEPTIONALLY POWERFUL; MITSUNOBU REACTIONS; ORGANIC-SYNTHESIS; RING EXPANSION; PIPECOLIC ACID; EFFICIENT Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/44593