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(−)-Frontalin: Synthesis using the Catalytic Enantioselective Addition of Dimethylzinc to a Ketone

✍ Scribed by Miguel Yus; Diego J. Ramón; Oscar Prieto

Book ID: 102177237
Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 99 KB
Volume: 2003
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300261

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✦ Synopsis

Abstract

The first enantioselective synthesis of (−)‐frontalin involving an enantioselective nucleophilic 1,2‐addition of dimethylzinc to a functionalized α,β‐unsaturated ketone, in the presence of titanium tetraisopropoxide and a substoichiometric amount of the chiral ligand 1,2‐trans‐bis(hydroxycamphorsulfonamido)cyclohexane (HOCSAC, 2) as the key step, is described. The enantiomeric excess is as high as 89%. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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