Diastereoselective synthesis of spirooxindole derivatives via biocatalytic domino reaction

A facile promiscuous reaction catalyzed by Acylase ‘Amano’ was developed for the preparation of spirooxindole derivatives. At the optimized reaction condition, the acylase-catalyzed domino reactions could provide a series of different spirooxindole products in moderate yields and good diastereoselec...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2015-01, Vol.71 (4), p.616-621
Main Authors: Liang, Yi-Ru, Chen, Xiao-Yang, Wu, Qi, Lin, Xian-Fu
Format: Article
Language:English
Subjects:
Acylase
Cascade chemical reactions
Derivatives
Diastereoselectivity
Domino reaction
Spirooxindole
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A facile promiscuous reaction catalyzed by Acylase ‘Amano’ was developed for the preparation of spirooxindole derivatives. At the optimized reaction condition, the acylase-catalyzed domino reactions could provide a series of different spirooxindole products in moderate yields and good diastereoselectivity. A chemo-enzymatic two-step process was also designed successfully, and several representative spirooxindole derivatives could be obtained in nearly quantitative yields. Additionally, one tentative mechanism for this enzyme-catalyzed process was proposed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.12.027