Synthesis of Chiral γ,γ-Disubstituted γ‑Butenolides via Direct Vinylogous Aldol Reaction of Substituted Furanone Derivatives with Aldehydes

Synthesis of Chiral γ,γ-Disubstituted γ‑Butenolides via Direct Vinylogous Aldol Reaction of Substituted Furanone Derivatives with Aldehydes

An organocatalyzed method for synthesizing chiral γ,γ-disubstituted γ-butenolides via direct vinylogous aldol reactions of γ-substituted β,γ-butenolides with aldehydes is reported. This reaction is catalyzed by a squaramide–sulfonamide organocatalyst to afford a range of anti-aldol adducts possessin...

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Veröffentlicht in:Organic letters 2019-04, Vol.21 (8), p.2606-2609
Hauptverfasser: Sakai, Takaaki, Hirashima, Shin-ichi, Matsushima, Yasuyuki, Nakano, Tatsuki, Ishii, Daiki, Yamashita, Yoshifumi, Nakashima, Kosuke, Koseki, Yuji, Miura, Tsuyoshi
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container_end_page 2609
container_issue 8
container_start_page 2606
container_title Organic letters
container_volume 21
creator Sakai, Takaaki
Hirashima, Shin-ichi
Matsushima, Yasuyuki
Nakano, Tatsuki
Ishii, Daiki
Yamashita, Yoshifumi
Nakashima, Kosuke
Koseki, Yuji
Miura, Tsuyoshi
description An organocatalyzed method for synthesizing chiral γ,γ-disubstituted γ-butenolides via direct vinylogous aldol reactions of γ-substituted β,γ-butenolides with aldehydes is reported. This reaction is catalyzed by a squaramide–sulfonamide organocatalyst to afford a range of anti-aldol adducts possessing vicinal quaternary and tertiary stereocenters with high to excellent enantioselectivities (reaching 95% ee). This is the first report of a successful stereoselective direct vinylogous aldol reaction of aldehydes with γ-substituted β,γ-butenolides.
doi_str_mv 10.1021/acs.orglett.9b00574
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title Synthesis of Chiral γ,γ-Disubstituted γ‑Butenolides via Direct Vinylogous Aldol Reaction of Substituted Furanone Derivatives with Aldehydes
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