Universität zu Köln

Brauns, Marcus, Mantel, Marvin, Schmauck, Julie, Guder, Marian ORCID: 0000-0002-7584-5855, Breugst, Martin ORCID: 0000-0003-0950-8858 and Pietruszka, Joerg (2017). Highly Enantioselective Allylation of Ketones: An Efficient Approach to All Stereoisomers of Tertiary Homoallylic Alcohols. Chem.-Eur. J., 23 (50). S. 12136 - 12141. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

Full text not available from this repository.

Abstract

An optimized protecting group for allylboronates allowed the use of ketones in order to synthesize all isomers of quaternary homoallylic alcohols with high enantioselectivities. All symmetric isomers of the allylboronate were prepared in high yields and diastereoselectivities using S(N)2' reactions. The improved reactivity of the novel protecting group was verified by following the reaction kinetics with H-1 NMR spectroscopy. Mechanistic studies using DFT calculations were conducted to investigate the new findings. Thus, the stereochemical outcome and enhanced reactivity can be rationalized.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Brauns, Marcus UNSPECIFIED UNSPECIFIED UNSPECIFIED Mantel, Marvin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmauck, Julie UNSPECIFIED UNSPECIFIED UNSPECIFIED Guder, Marian UNSPECIFIED orcid.org/0000-0002-7584-5855 UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Pietruszka, Joerg UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-217916
DOI:	10.1002/chem.201701740
Journal or Publication Title:	Chem.-Eur. J.
Volume:	23
Number:	50
Page Range:	S. 12136 - 12141
Date:	2017
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
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 ASYMMETRIC ALLYLBORATION; LEWIS-ACID; SUBSTITUENT CONSTANTS; ALDEHYDES; REAGENTS; STEREOCENTERS; CONSTRUCTION; ACTIVATION; BORON Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/21791