Brauns, Marcus, Muller, Frederic, Guelden, Daniel, Boese, Dietrich, Frey, Wolfgang, Breugst, Martin ORCID: 0000-0003-0950-8858 and Pietruszka, Joerg (2016). Enantioselective Catalysts for the Synthesis of alpha-Substituted Allylboronates-An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols. Angew. Chem.-Int. Edit., 55 (4). S. 1548 - 1553. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

The use of a convenient protecting group for boronates allows a selective, catalyzed S(N)2' reaction to generate allylboronates which are applied for the synthesis of enantio-merically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Brauns, MarcusUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Muller, FredericUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Guelden, DanielUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Boese, DietrichUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Frey, WolfgangUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Breugst, MartinUNSPECIFIEDorcid.org/0000-0003-0950-8858UNSPECIFIED
Pietruszka, JoergUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-287043
DOI: 10.1002/anie.201509198
Journal or Publication Title: Angew. Chem.-Int. Edit.
Volume: 55
Number: 4
Page Range: S. 1548 - 1553
Date: 2016
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3773
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
HYDROID SOLANDERIA-SECUNDA; ASYMMETRIC-SYNTHESIS; CONSTANOLACTONE-B; SOLANDELACTONES-A; ONE-POT; REAGENTS; NEOHALICHOLACTONE; OXYLIPINS; ALDEHYDES; ESTERSMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/28704

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