Universität zu Köln

Harnying, Wacharee, Neudoerfl, Joerg-M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2017). Catalytic Prins Reaction Effected by Molecular Iodine in the Presence of Bis(trifluoromethanesulfonyl)imide Salts. Synthesis, 49 (2). S. 269 - 275. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

The Prins reaction is an efficient method for the direct generation of 1,3-dioxanes from alkenes and aldehydes. As first published in 2008, this process can be effected by stoichiometric amounts of molecular iodine. We herein report a catalytic protocol allowing the use of iodine at low loading (0.5-5 mol%), smoothly effecting the condensation of styrenes with aliphatic aldehydes to rac-1,3-dioxanes. Moreover, this mild catalytic system effects the isomerization of the 1,3-dioxane products to the thermodynamically favored one. As a result, substituted rac-1,3-dioxanes were prepared in high yields (up to 92%), and with high diastereoselectivities (d.r. up to 82: 18). For the application of iodine in catalytic amounts, the addition of pyridinium bis(trifluoromethanesulfonyl)imide (TFSI) salts in a 1: 1 ratio to iodine is the key to success.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Harnying, Wacharee UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-247533
DOI:	10.1055/s-0036-1588367
Journal or Publication Title:	Synthesis
Volume:	49
Number:	2
Page Range:	S. 269 - 275
Date:	2017
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-210X
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 ION-EXCHANGING RESINS; AROMATIC ALKENES; 1,3-DIOXANE DERIVATIVES; MODULAR SYNTHESIS; CONDENSATION; ALDEHYDES; EFFICIENT; COMBINATION; EXTENSION; STYRENES Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/24753