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N-alpha-benzyloxyacetyl derivatives of (S)-4-benzyl-5,5-dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected alpha,beta-dihydroxyaldehydes

Abstract:

α-Dibenzylamino- and α-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the α-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding α-amino-β-hydroxy methyl ester or α-amino-β-hydroxyaldehyde p...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2004.05.123

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Hunter, IA More by this author
Nicholson, RL More by this author
Roberts, PM More by this author
Savory, ED More by this author
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Journal:
TETRAHEDRON
Volume:
60
Issue:
35
Pages:
7553-7577
Publication date:
2004-08-23
DOI:
ISSN:
0040-4020
URN:
uuid:398bfee2-f2a5-4f8d-90cd-4f61ff48edad
Source identifiers:
110578
Local pid:
pubs:110578
Language:
English
Keywords:

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