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Paper | Regular issue | Vol 91, No. 12, 2015, pp.2295-2305
Published online, 27th November, 2015
DOI: 10.3987/COM-15-13324
P-Stereogenic Diphosphacrowns: Facile Incorporation of Aromatic Rings

Ryosuke Kato, Hiroyuki Watanabe, Yasuhiro Morisaki,* and Yoshiki Chujo*

*Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan

Abstract

P-Stereogenic diphosphacrowns containing naphthalene and pyridine rings were synthesized. Facile incorporation of aromatic rings, and chains of different lengths, into the diphosphacrown skeleton was achieved by altering the electrophile in our previously reported synthetic method. Pyridine-containing diphosphacrown exhibited chiral recognition ability for chiral ammonium salts and carboxylic acids. This is the first example of chiral recognition using P-stereogenic diphosphacrowns. 1H and 31P NMR spectra indicated that the nitrogen, oxygen, and chiral phosphorus atoms contributed to the chiral recognition cooperatively.