The generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.
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Univ Paris Sud 11, Lab Catalyse Mol, ICMMO, UMR 8182, F-91405 Orsay, FranceUniv Paris Sud 11, Lab Catalyse Mol, ICMMO, UMR 8182, F-91405 Orsay, France
Aupoix, Audrey
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Bournaud, Chloee
Vo-Thanh, Giang
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Univ Paris Sud 11, Lab Catalyse Mol, ICMMO, UMR 8182, F-91405 Orsay, FranceUniv Paris Sud 11, Lab Catalyse Mol, ICMMO, UMR 8182, F-91405 Orsay, France