Issue 63, 2014

Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

Abstract

A highly efficient catalytic asymmetric Diels–Alder reaction between 3-vinylindoles and methyleneindolinones has been achieved using chiral N,N′-dioxide–Ni(II) complexes as the catalysts. A wide variety of substrates were readily tolerated, generating exclusively the corresponding exo-carbazolespirooxindole derivatives in excellent yields with high enantiomeric excesses (up to 98% yield, >99 : 1 d.r., and 98% ee) under mild reaction conditions.

Graphical abstract: Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

Supplementary files

Article information

Article type
Communication
Submitted
28 Apr 2014
Accepted
13 Jun 2014
First published
26 Jun 2014

Chem. Commun., 2014,50, 8794-8796

Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

H. Zheng, P. He, Y. Liu, Y. Zhang, X. Liu, L. Lin and X. Feng, Chem. Commun., 2014, 50, 8794 DOI: 10.1039/C4CC03135K

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