‘Transmitted’ remote double diastereoselection effects on the asymmetric reduction of β-boronate oxime ethers

Remote asymmetric induction in the reduction of a homochiral β-boronate oxime ether to the corresponding amine failed to provide asymmetric induction with achiral reducing agents, but use of a chiral reducing agent produced extreme double diastereoselection effects which show that remote asymmetry c...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 14; pp. 2457 - 2461
Main Authors Sailes, Helen E., Watts, John P., Whiting, Andrew
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.04.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETO ESTERS
REAGENTS
STEREOCONTROL
AMINO ACIDS
COMPLEXES
INDUCTION
CENTERS
DERIVATIVES
AUXILIARY
HYDRIDE
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Summary:Remote asymmetric induction in the reduction of a homochiral β-boronate oxime ether to the corresponding amine failed to provide asymmetric induction with achiral reducing agents, but use of a chiral reducing agent produced extreme double diastereoselection effects which show that remote asymmetry can be ‘transmitted’ by suitable choice of a ‘partner’ molecule.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00179-9