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Org Lett. 2012 Sep 21;14(18):4706-9. Epub 2012 Sep 7.

Tröger's base twisted amides: endo functionalization and synthesis of an inverted crown ether.

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1
Centre for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund, Sweden.

Abstract

Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.

PMID:
22958089
DOI:
10.1021/ol302022y
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