Literature DB >> 28287726

Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3-Amideoxindoles and α,β-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-γ-lactams.

Peng Yang1,2, Xiao Wang1,2, Feng Chen1,2, Zheng-Bing Zhang1,2, Chao Chen1,2, Lin Peng1, Li-Xin Wang1.   

Abstract

The first organocatalytic enantioselective Michael/cyclization domino reaction between 3-amideoxindoles and α,β-unsaturated aldehydes is described. After sequential oxidation with pyridinium chlorochromate, a direct and one-pot preparation of highly sterically hindered spirocyclic oxindole-γ-lactams was achieved in 51-81% yields with 75-97% ee and ≤80/20 dr.

Entities:  

Year:  2017        PMID： 28287726     DOI： 10.1021/acs.joc.6b03090

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles.

Authors:  Ziwei Zhong; Zhijie Xiao; Xiaohua Liu; Weidi Cao; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

2.  Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors:  Amarendar Reddy Maddirala; Peter R Andreana
Journal:  Beilstein J Org Chem       Date:  2018-04-18       Impact factor: 2.883
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.