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

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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:
CreatorsEmailORCIDORCID Put Code
Brauns, MarcusUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Mantel, MarvinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmauck, JulieUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Guder, MarianUNSPECIFIEDorcid.org/0000-0002-7584-5855UNSPECIFIED
Breugst, MartinUNSPECIFIEDorcid.org/0000-0003-0950-8858UNSPECIFIED
Pietruszka, JoergUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
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: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ASYMMETRIC ALLYLBORATION; LEWIS-ACID; SUBSTITUENT CONSTANTS; ALDEHYDES; REAGENTS; STEREOCENTERS; CONSTRUCTION; ACTIVATION; BORONMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/21791

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