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

Abstract:
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.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Ichihara, O More by this author
Journal:
TETRAHEDRON LETTERS
Volume:
39
Issue:
33
Pages:
6045-6048
Publication date:
1998-08-13
DOI:
ISSN:
0040-4039
URN:
uuid:00d352cb-b141-4d78-a8e7-a84cd4ce491b
Source identifiers:
110630
Local pid:
pubs:110630
Language:
English

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