Universität zu Köln

Kang, Young Ku, Chen, Weijie, Breugst, Martin ORCID: 0000-0003-0950-8858 and Seidel, Daniel ORCID: 0000-0001-6725-111X (2015). Asymmetric Redox-Annulation of Cyclic Amines. J. Org. Chem., 80 (19). S. 9628 - 9641. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

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Abstract

Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycydic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Kang, Young Ku UNSPECIFIED UNSPECIFIED UNSPECIFIED Chen, Weijie UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Seidel, Daniel UNSPECIFIED orcid.org/0000-0001-6725-111X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-390041
DOI:	10.1021/acs.joc.5b01384
Journal or Publication Title:	J. Org. Chem.
Volume:	80
Number:	19
Page Range:	S. 9628 - 9641
Date:	2015
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6904
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language C-H BOND; MICHAEL ADDITIONS; TERMINAL ALKYNES; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT ORGANOCATALYSTS; ALPHA-AMINATION; FUNCTIONALIZATION; ALDEHYDES; CONSTRUCTION; STRATEGY Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/39004