Universität zu Köln

Breugst, Martin ORCID: 0000-0003-0950-8858 and Houk, K. N. (2014). Computational Analysis of Cyclophane-Based Bisthiourea-Catalyzed Henry Reactions. J. Org. Chem., 79 (13). S. 6302 - 6310. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

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Abstract

The Henry reaction between benzaldehyde and nitromethane catalyzed by a cyclophane-based bisthiourea has been studied with density functional theory [M06-2X-D3/def2-TZVPP/IEFPCM// TPSS-D2/6-31G(d)/IEFPCM]. The results of our study reveal that the transformation involves the reaction of a thiourea nitronate complex with the uncoordinated aldehyde. On the basis of our calculations, the formation of the major stereoisomer is kinetically preferred. Employing smaller model systems, we show that the observed stereoselectivity arises primarily from differences in hydrogen bonding in diastereomeric transition states.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Houk, K. N. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-434049
DOI:	10.1021/jo501227m
Journal or Publication Title:	J. Org. Chem.
Volume:	79
Number:	13
Page Range:	S. 6302 - 6310
Date:	2014
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 DENSITY-FUNCTIONAL THEORY; DIELS-ALDER REACTIONS; DIASTEREOSELECTIVE SYNTHESIS; EQUILIBRIUM ACIDITIES; BOND DONORS; METAL-FREE; M06 SUITE; ORGANOCATALYST; RECOGNITION; THIOUREAS Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/43404