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

Journal article

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.

Authors: Davies, S; Ichihara, O

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 39
• Issue: 33
• Pages: 6045-6048
• Publication date: 1998-08-13
• DOI: 10.1016/S0040-4039(98)01193-9
• ISSN: 0040-4039
• Language: English