Enantio- and diastereoselective synthesis of β-substituted-δ-aminoboronic esters from nitriles

The first stereocontrolled synthesis of the title δ-aminoboronic esters—proceeding from commercially available nitriles—via a reduction, Brown’s ‘allyl’ boration reaction, a Boc-protection, a hydroboration, an oxidative elimination of α-pinene, and an esterification reaction, has been reported in ex...

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Bibliographic Details
Published in:Tetrahedron letters 2013-09, Vol.54 (36), p.4830-4833
Main Authors: Ramachandran, P. Veeraraghavan, Mitsuhashi, Wataru, Biswas, Debanjan, Nicponski, Daniel R.
Format: Article
Language:English
Subjects:
Allylboration
Amino-boronic ester
Crotylboration
Methoxyallylboration
Nitriles
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Summary:The first stereocontrolled synthesis of the title δ-aminoboronic esters—proceeding from commercially available nitriles—via a reduction, Brown’s ‘allyl’ boration reaction, a Boc-protection, a hydroboration, an oxidative elimination of α-pinene, and an esterification reaction, has been reported in excellent enantio- and diastereoselectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.06.076