Chelation-Controlled Additions to α‑Silyloxy Aldehydes: An Autocatalytic Approach

Chelation-Controlled Additions to α‑Silyloxy Aldehydes: An Autocatalytic Approach

The Felkin–Anh model has been widely accepted to describe stereochemical outcomes in nucleophilic additions to α-silyloxy carbonyl compounds. Herein, it is demonstrated that chelation-controlled additions can be performed using dialkylzinc reagents in the presence of chlorotrimethylsilane with good...

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Veröffentlicht in:Organic letters 2013-12, Vol.15 (24), p.6174-6177
Hauptverfasser: Raffier, Ludovic, Stanton, Gretchen R, Walsh, Patrick J
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemical synthesis
Alcohols - chemistry
Aldehydes - chemistry
Catalysis
Molecular Conformation
Stereoisomerism
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Zusammenfassung:The Felkin–Anh model has been widely accepted to describe stereochemical outcomes in nucleophilic additions to α-silyloxy carbonyl compounds. Herein, it is demonstrated that chelation-controlled additions can be performed using dialkylzinc reagents in the presence of chlorotrimethylsilane with good to excellent diastereoselectivities. Ethyl zinc chloride, the Lewis acid responsible for promoting chelation, is generated in situ in an autocatalytic fashion. This approach circumvents its use in stoichiometric amounts.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4030259