Journal Article

FZJ-2020-03836

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones

Drennhaus, T.FZJ* ; Öhler, L.FZJ* ; Djalali, S. ; Höfmann, S. ; Müller, C. ; Pietruszka, J. (Corresponding author)FZJ* ; Worgull, D.FZJ*

2020
Wiley-VCH Weinheim

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Please use a persistent id in citations: http://hdl.handle.net/2128/25837  doi:10.1002/adsc.202000039

Abstract: An ammonium ylide mediated access towards trans‐β,γ‐disubstituted, all‐trans‐α,β,γ‐trisubstituted, and α,α,β,γ‐tetrasubstituted γ‐butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α‐bromo carbonyl compounds, γ‐butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO‐mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R, 4R)‐β,γ‐disubstituted and (2R, 3R, 4R)‐α,β,γ‐trisubstituted γ‐butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration.

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Contributing Institute(s):

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

Research Program(s):

1. 581 - Biotechnology (POF3-581) (POF3-581)

Appears in the scientific report 2020

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Database coverage:
; ; ; Chemical Reactions ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; DEAL Wiley ; Ebsco Academic Search ; Essential Science Indicators ; IF >= 5 ; Index Chemicus ; JCR ; NCBI Molecular Biology Database ; SCOPUS ; Science Citation Index ; Science Citation Index Expanded ; Web of Science Core Collection

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