Asymmetric [3 + 2] annulation of N-protected isatins with but-3-yn-2-one catalyzed by DIOP: facile creation of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione

Zhong Lian; Min Shi

doi:10.1039/c2ob25801c

Asymmetric [3 + 2] annulation of N-protected isatins with but-3-yn-2-one catalyzed by DIOP: facile creation of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione

Org Biomol Chem. 2012 Oct 28;10(40):8048-50. doi: 10.1039/c2ob25801c.

Authors

Zhong Lian¹, Min Shi

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P.R. China.

PMID: 22930008
DOI: 10.1039/c2ob25801c

Abstract

DIOP catalyzed highly enantioselective [3 + 2] annulation of N-protected isatins with but-3-yn-2-one has been disclosed, allowing the synthesis of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione in moderate yields along with good to high enantioselectivities under mild conditions.

Publication types

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

MeSH terms

Alkynes / chemistry*
Catalysis
Cyclization
Dioxolanes / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Isatin / chemistry*
Ketones / chemistry*
Molecular Structure
Phosphines / chemistry*
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Alkynes
Dioxolanes
Indoles
Ketones
Phosphines
Spiro Compounds
Isatin