Highly enantioselective one-pot synthesis of spirocyclopentaneoxindoles containing the oxime group by organocatalyzed Michael addition/ISOC/fragmentation sequence

Xiang Li; Ying-Mei Li; Fang-Zhi Peng; Shou-Tao Wu; Ze-Qian Li; Zhong-Wen Sun; Hong-Bin Zhang; Zhi-Hui Shao

doi:10.1021/ol2024955

Highly enantioselective one-pot synthesis of spirocyclopentaneoxindoles containing the oxime group by organocatalyzed Michael addition/ISOC/fragmentation sequence

Org Lett. 2011 Dec 2;13(23):6160-3. doi: 10.1021/ol2024955. Epub 2011 Nov 3.

Authors

Xiang Li¹, Ying-Mei Li, Fang-Zhi Peng, Shou-Tao Wu, Ze-Qian Li, Zhong-Wen Sun, Hong-Bin Zhang, Zhi-Hui Shao

Affiliation

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.

PMID: 22050288
DOI: 10.1021/ol2024955

Abstract

A highly diastereo- and enantioselective organocatalytic protocol for the synthesis of biologically important spirocyclopentaneoxindoles containing the oxime functional group from easily accessible 3-allyl-substituted oxindoles and nitroolefins has been developed by a one-pot Michael addition/ISOC/fragmentation sequence.

Publication types

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

MeSH terms

Catalysis
Cyclization
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Oximes / chemistry*
Oxindoles
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Cyclopentanes
Indoles
Oximes
Oxindoles
Spiro Compounds
2-oxindole