Asymmetric intramolecular cyclobutane formation via photochemical reaction of N,N-diallyl-2-quinolone-3-carboxamide using a chiral crystalline environment

Fumitoshi Yagishita; Masami Sakamoto; Takashi Mino; Tsutomu Fujita

doi:10.1021/ol2028652

Asymmetric intramolecular cyclobutane formation via photochemical reaction of N,N-diallyl-2-quinolone-3-carboxamide using a chiral crystalline environment

Org Lett. 2011 Dec 2;13(23):6168-71. doi: 10.1021/ol2028652. Epub 2011 Nov 9.

Authors

Fumitoshi Yagishita¹, Masami Sakamoto, Takashi Mino, Tsutomu Fujita

Affiliation

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

PMID: 22070633
DOI: 10.1021/ol2028652

Abstract

Crystal structures and photochemical reactions of three N,N-diallyl-2-quinolone-3-carboxamides were investigated. One quinolonecarboxamide afforded chiral crystals of a P2(1) crystal system by spontaneous crystallization, and the molecular chirality in the crystal was effectively transferred to cyclobutane in 96% ee by an intramolecular 2 + 2 photocycloaddition reaction in the solid state.