Home > Publications database > Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones > print

001     885453
005     20210130010411.0
024 7 _ |a 10.1002/adsc.202000039
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100 1 _ |a Drennhaus, Till
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245 _ _ |a Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones
260 _ _ |a Weinheim
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520 _ _ |a 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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700 1 _ |a Öhler, Laura
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700 1 _ |a Djalali, Saveh
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700 1 _ |a Höfmann, Svenja
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700 1 _ |a Müller, Clemens
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700 1 _ |a Pietruszka, Jörg
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700 1 _ |a Worgull, Dennis
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773 _ _ |a 10.1002/adsc.202000039
|g Vol. 362, no. 12, p. 2385 - 2396
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|t Advanced synthesis & catalysis
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