N-Heterocyclic carbene-catalyzed [3 + 2] annulation of bromoenals with 3-aminooxindoles: highly enantioselective synthesis of spirocyclic oxindolo-γ-lactams

Kun-Quan Chen; Yao Li; Chun-Lin Zhang; De-Qun Sun; Song Ye

doi:10.1039/c5ob02466h

N-Heterocyclic carbene-catalyzed [3 + 2] annulation of bromoenals with 3-aminooxindoles: highly enantioselective synthesis of spirocyclic oxindolo-γ-lactams

Org Biomol Chem. 2016 Feb 14;14(6):2007-14. doi: 10.1039/c5ob02466h.

Authors

Kun-Quan Chen¹, Yao Li¹, Chun-Lin Zhang², De-Qun Sun³, Song Ye²

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. songye@iccas.ac.cn and Marine College, Shandong University at Weihai, 180 Wenhua West Road, Weihai 264209, China. dequn.sun@sdu.edu.cn.
² Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. songye@iccas.ac.cn.
³ Marine College, Shandong University at Weihai, 180 Wenhua West Road, Weihai 264209, China. dequn.sun@sdu.edu.cn.

PMID: 26755065
DOI: 10.1039/c5ob02466h

Abstract

The chiral N-heterocyclic carbene-catalyzed [3 + 2] annulation of α-bromoenals and 3-aminooxindoles was developed, giving the corresponding spirocyclic oxindolo-γ-lactams in good yields with high diastereoselectivities and enantioselectivities.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Heterocyclic Compounds / chemistry*
Hydrocarbons, Brominated / chemistry*
Indoles / chemistry*
Lactams / chemical synthesis*
Lactams / chemistry
Methane / analogs & derivatives*
Methane / chemistry
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry

Substances

Heterocyclic Compounds
Hydrocarbons, Brominated
Indoles
Lactams
Spiro Compounds
carbene
Methane