Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives

Shuang Zhang; Yong-Chun Luo; Xiu-Qin Hu; Zhu-Yin Wang; Yong-Min Liang; Peng-Fei Xu

doi:10.1021/acs.joc.5b00961

Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives

J Org Chem. 2015 Jul 17;80(14):7288-94. doi: 10.1021/acs.joc.5b00961. Epub 2015 Jul 2.

Authors

Shuang Zhang¹, Yong-Chun Luo¹, Xiu-Qin Hu¹, Zhu-Yin Wang², Yong-Min Liang¹, Peng-Fei Xu¹

Affiliations

¹ †State Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
² ‡College of Mechanics and Materials, Hohai University, Nanjing 210098, P. R. China.

PMID: 26102600
DOI: 10.1021/acs.joc.5b00961

Abstract

An efficient cinchona alkaloid-derived amine catalyzed asymmetric [4 + 2] cycloaddition is successfully developed. 4H-Pyran fused pyrrolin-2-one products are readily obtained in moderate to high yields with good enantioselectivites by employing allene ketones and 2,3-dioxopyrrolidine derivatives as substrates.

Publication types

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

MeSH terms

Alkadienes / chemistry*
Amines / chemistry*
Catalysis
Cycloaddition Reaction
Ketones / chemistry*
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Pyrrolidines / chemistry*
Stereoisomerism

Substances

Alkadienes
Amines
Ketones
Pyrans
Pyrrolidines