Journal Article

FZJ-2017-00828

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Synthesis of Alkenylboronic Esters: An Alternative Route to Trisubstituted Homoallylic Alcohols

Gehrke, Y. ; Berg, C. A. ; Vahabi, R. ; Pietruszka, J. (Corresponding author)FZJ*

2016
Wiley-VCH Verl. Weinheim

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Please use a persistent id in citations: doi:10.1002/ejoc.201600139

Abstract: New alkenylboronic esters were synthesised from halo-substituted alkenylboronic esters through cross-coupling reactions. Upon Johnson rearrangement, enantiomerically pure allylboronates bearing a stereogenic centre in the position α to the boron moiety were obtained in moderate yield (53 %; 29 % over six steps from the protected propargylic alcohols). The products of these reactions were separable by medium-pressure liquid chromatography, and could be used in highly stereoselective allylation reactions to synthesise enantiomerically enriched homoallylic alcohols containing a 1,1,2-trisubstituted (Z)-configured double bond.

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Contributing Institute(s):

1. Institut für Bioorganische Chemie (HHUD) (IBOC)
2. Biotechnologie (IBG-1)

Research Program(s):

1. 583 - Innovative Synergisms (POF3-583) (POF3-583)

Appears in the scientific report 2016

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Database coverage:
; Current Contents - Physical, Chemical and Earth Sciences ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; No Authors Fulltext ; SCOPUS ; Science Citation Index ; Science Citation Index Expanded ; Thomson Reuters Master Journal List ; Web of Science Core Collection

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