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Highly stereoselective generation of α-pyrones displaying four contiguous stereogenic centers

✍ Scribed by Frédéric Marion; Sandrine Calvet; Christine Courillon; Max Malacria

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
60 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

We report here an efficient one-pot diastereoselective procedure which transforms silylated vinyloxiranes 2 into enantiomerically pure tetrasubstituted d-lactones 7, 10. This transformation includes four steps: palladium(0)-catalyzed rearrangement/alkylation-lactonization/1,4-conjugated addition/electrophilic trapping of the intermediary enolate. These reactions allow efficient control of four contiguous stereogenic centers, and even of a fifth one when the electrophile is the prochiral benzaldehyde.

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✍ Keisuke Suzuki; Eiji Katayama; Katsuhiko Tomooka; Takashi Matsumoto; Gen-ichi Ts 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 247 KB

AZZ four diastereomers of chiral alcohol 2 with three contiguous chiral centers were stereoselectiveZy prepared via diastere~selective addition of nucleophiles (crotyl metal or H-J to n-methyZ-B,y-unsaturated carbonyl compounds 1.