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

Author:
Sakai, Takaaki, Hirashima, Shin-ichi, Matsushima, Yasuyuki, Nakano, Tatsuki, Ishii, Daiki, Yamashita, Yoshifumi, Nakashima, Kosuke, Koseki, Yuji, Miura, Tsuyoshi
Source:
Organic letters 2019 v.21 no.8 pp. 2606-2609
ISSN:
1523-7052
Subject:
aldehydes, chemical reactions, chemical structure, enantioselectivity, organocatalysts
Abstract:
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.
Agid:
6375925