4.4 Article

Organocatalytic domino sequence to asymmetrically access spirocyclic oxindole-α-methylene-γ-lactams

Journal

TETRAHEDRON
Volume 89, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132163

Keywords

Asymmetric organocatalysis; Allylic alkylation-lactamization; Morita-Baylis-Hillman carbonates; Spirooxindole

Funding

  1. National Natural Science Foundation of China [21576296, 21776318, 81703365, 22003077]
  2. Natural Science Foundation of Hunan Province [2018JJ3868, 2017JJ3401]
  3. Central South University

Ask authors/readers for more resources

A new synthetic method has been developed for the efficient synthesis of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams. The method utilizes Morita-Baylis-Hillman carbonates as substrates and quinidine derivatives as catalysts to achieve stereoselective control over the products. This research broadens the application of Morita-Baylis-Hillman carbonates in the asymmetric construction of spirocyclic oxindoles.
An asymmetric allylic alkylation-lactamization domino sequence of 3-aminooxindoles with Morita-Baylis-Hillman carbonates catalyzed by quinidine derivative (beta-ICD) was developed. And a series of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams have been facilely prepared in good yields and stereoselectivities. This developed protocol would broaden the utilization of Morita-Baylis-Hillman carbonates in asymmetric construction of spirocyclic oxindoles. (C) 2021 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available