Highly enantioselective catalytic 1,3-dipolar cycloaddition involving 2,3-allenoate dipolarophiles

Jie Yu; Long He; Xiao-Hua Chen; Jin Song; Wei-Jie Chen; Liu-Zhu Gong

doi:10.1021/ol9020964

Highly enantioselective catalytic 1,3-dipolar cycloaddition involving 2,3-allenoate dipolarophiles

Org Lett. 2009 Nov 5;11(21):4946-9. doi: 10.1021/ol9020964.

Authors

Jie Yu¹, Long He, Xiao-Hua Chen, Jin Song, Wei-Jie Chen, Liu-Zhu Gong

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

PMID: 19813752
DOI: 10.1021/ol9020964

Abstract

A bisphosphoric acid-catalyzed 1,3-dipolar cycloaddition of buta-2,3-dienoates with azomethine ylides yields 3-methylenepyrrolidine derivatives with excellent enantioselectivity (up to 97% ee).

Publication types

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

MeSH terms

Azo Compounds / chemistry*
Catalysis
Cyclization
Molecular Structure
Phosphoric Acids / chemistry*
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism
Thiosemicarbazones / chemistry*

Substances

Azo Compounds
Phosphoric Acids
Pyrrolidines
Thiosemicarbazones
azomethine