FACILE SYNTHESIS OF SPIROOXINDOLES VIA AN ENANTIOSELECTIVE ORGANOCATALYZED SEQUENTIAL REACTION OF OXINDOLES WITH YNONE

The reaction of oxindole la with phenylprop-2-yn-l-one (2a) was promoted by the chiral multifunctional phosphine catalyst 4a derived from (S)-valine, giving spirooxindole 3a in good yield and high enantioselectivity. The obtained spirooxindole forms a common scaffold of a vast number of natural prod...

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Bibliographic Details
Published inHeterocycles Vol. 95; no. 2; pp. 761 - 767
Main Authors Takizawa, Shinobu, Kishi, Kenta, Kusaba, Miki, Bai Jianfei, Suzuki, Takeyuki, Sasai, Hiroaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Oxindole
STEREOGENIC CARBON CENTER
C,N-CYCLIC AZOMETHINE IMINES
Organocatalyst
Domino Reaction
BAYLIS-HILLMAN REACTION
CHIRAL SPIRO LIGANDS
CASCADE REACTION
CYCLOADDITION
Spiro Compound
ALLENOATES
CATALYZED ASYMMETRIC REACTIONS
ACCESS
DOUBLE-MICHAEL REACTIONS
Online AccessGet more information

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Summary:The reaction of oxindole la with phenylprop-2-yn-l-one (2a) was promoted by the chiral multifunctional phosphine catalyst 4a derived from (S)-valine, giving spirooxindole 3a in good yield and high enantioselectivity. The obtained spirooxindole forms a common scaffold of a vast number of natural products exhibiting various biological activities.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-16-S(S)86