Organic Letters 2012-12-21

Synthesis and functionalization of inherently chiral tetraoxacalix[2]arene[2]pyridines.

Shuai Pan, De-Xian Wang, Liang Zhao, Mei-Xiang Wang

Index: Org. Lett. 14(24) , 6254-7, (2012)

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Abstract

Inherently chiral tetraoxacalix[2]arene[2]pyridines containing C(2) symmetry were synthesized efficiently from a macrocyclic condensation reaction of resorcinol derivatives with 2,6-dichloro-3-nitropyridine in a one-pot reaction manner, while tetraoxacalix[2]arene[2]pyridine with an ABCD-substitution pattern was prepared in a good yield by means of a stepwise fragment coupling approach. Postmacrocyclization chemical manipulations led to functionalized tetraoxacalix[2]arene[2]pyridines. A racemic sample was resolved into enantiopure (+)- and (-)-inherently chiral compounds.