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Asymmetric synthesis of homochiral differentially protected bis-beta-amino acid scaffolds

Abstract:

A strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2 symmetric scaffolds via selective N-benzyl or N-allyl deprotection, enabling regio-, st...

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Publication status:
Published

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON More from this journal
Volume:
58
Issue:
23
Pages:
4629-4642
Publication date:
2002-06-03
DOI:
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:110590
UUID:
uuid:c8db3dde-bb5d-4568-a460-7dec48569ad4
Local pid:
pubs:110590
Source identifiers:
110590
Deposit date:
2012-12-19

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