Asymmetric synthesis of benzofuryl β-amino alcohols by the transfer hydrogenation of α-functionalized ketones

The asymmetric transfer hydrogenation of representative benzofuryl α-sulfonyloxy ketones and N-protected α-amino ketones with an azeotropic mixture of formic acid/triethylamine, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5), afforded the corresponding 1,2-diol monosulfonates and N-substituted β-amino alcoh...

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Bibliographic Details
Published in:Tetrahedron 2017-07, Vol.73 (27-28), p.3883-3897
Main Authors: Tafelska-Kaczmarek, Agnieszka, Krzemiński, Marek P., Ćwiklińska, Marta
Format: Article
Language:English
Subjects:
Amino alcohols
Amino ketones
Asymmetric synthesis
Benzofuran
Transfer hydrogenation
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Summary:The asymmetric transfer hydrogenation of representative benzofuryl α-sulfonyloxy ketones and N-protected α-amino ketones with an azeotropic mixture of formic acid/triethylamine, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5), afforded the corresponding 1,2-diol monosulfonates and N-substituted β-amino alcohols in high yields and with enantioselectivities up to 99%. Transformation of the reduction products to the chiral benzofuryl β-amino alcohols possessing a primary amine group is also described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.05.059