Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams

Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams

A variety of N,N-diprotected β-amino esters, prepared by highly diastereoselective conjugate addition of chiral lithium amides, were selectively mono-deprotected under either reductive (hydrogenolysis) or oxidative (DDQ or CAN) conditions. Combined with these deprotection methods, lithium (α-methylb...

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Autori principali: Davies, S, Ichihara, O
Natura: Journal article
Lingua:English
Pubblicazione: 1998
Descrizione
Riassunto:A variety of N,N-diprotected β-amino esters, prepared by highly diastereoselective conjugate addition of chiral lithium amides, were selectively mono-deprotected under either reductive (hydrogenolysis) or oxidative (DDQ or CAN) conditions. Combined with these deprotection methods, lithium (α-methylbenzyl)(3,4-dimethoxybenzyl) amide 2 can be used as an efficient differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acid and β-lactam derivatives.

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