N-heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole-Reference-Cited by-同舟云学术

N-heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole

Published:2015 Issue:6 Volume:13 Page:1829-1835
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Xie Yuanwei¹²³⁴⁵,Que Yonglei¹²³⁴⁵,Li Tuanjie¹²³⁴⁵,Zhu Ling¹²³⁴⁵,Yu Chenxia¹²³⁴⁵,Yao Changsheng¹⁶³⁷⁵

Affiliation:

1. School of Chemistry and Chemical Engineering

2. Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials

3. Jiangsu Normal University

4. Xuzhou 221116

5. P. R. China

6. Key Laboratory of Biotechnology for Medicinal Plant

7. Xuzhou

Abstract

A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon with high diastereoselectivies.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/OB/C4OB01706D

Reference93 articles.

1. Carbene Catalysts

2. N-Heterocyclic Carbene Catalyzed Domino Reactions

3. Cooperative Lewis acid/N-heterocyclic carbene catalysis

4. Stereoselective Synthesis of Bicyclic Tertiary Alcohols with Quaternary Stereocenters via Intramolecular Crossed Benzoin Reactions Catalyzed by N-Heterocyclic Carbenes

5. Asymmetric Synthesis of Functionalized Cyclopentanones via a Multicatalytic Secondary Amine/N-Heterocyclic Carbene Catalyzed Cascade Sequence

Cited by 49 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. NHC‐Catalyzed Enantioselective Transformations Involving α‐Bromoenals;The Chemical Record;2024-04-08

2. Proline-Catalyzed Diastereoselective Synthesis of Dihydroquinolinyl-Spirooxindole via Aza-Michael/Aldol Reaction;Synthesis;2023-06-22

3. Chiral NHC‐Catalyzed [4+2] Cycloadditions: Highly Diastereo/Enantioselective Access to Spiro[cyclohex‐4‐ene‐1,3′‐indoles] and DFT Calculations;Chemistry – A European Journal;2023-03-15

4. Stereoselective N-Heterocyclic-Carbene-Catalyzed Formal [4 + 2] Cycloaddition: Access to Chiral Heterocyclic Cyclohexenones;Organic Letters;2023-01-03

5. N-Heterocyclic carbene catalyzed C-acylation reaction for access to linear aminoenones;Chinese Chemical Letters;2023-01