Diastereoselective ABB′ Three-Component Synthesis of Highly Functionalized Spirooxindoles Bearing Five Consecutive Asymmetric Carbons
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https://figshare.com/articles/dataset/Diastereoselective_ABB_Three-Component_Synthesis_of_Highly_Functionalized_Spirooxindoles_Bearing_Five_Consecutive_Asymmetric_Carbons/7877855
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资源简介:
The synthesis of spirooxindoles bearing
tetrahydro-4H-cyclopenta[b]furan
framework was established starting
from isatin-derived aldehydes and 2 equiv of 1,3-dicarbonyl compounds
involving a piperidine-catalyzed ABB′ three-component domino
process. This reaction was highly diastereoselective affording a single
diastereomer of spirooxindoles with five consecutive asymmetric carbons
including spiro and tetrasubstituted carbon centers. In addition,
this waste-free (−2H2O) reaction showed high atom
economy and step economy by creating four new bonds, including three
C–C bonds and one C–O bond, and two rings (one carbo-
and one heterocyclic) in a single operation. The mechanism of this
three-component domino process involved sequential Knoevenagel condensation–Michael
addition–intramolecular oxa-Michael addition–intramolecular
aldol reactions.
创建时间:
2019-03-21



