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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 23
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Original Articles

Synthesis of Optically Active Aromatic Ether Ketone Macrocycles Containing 2,2′-Dimethoxy-1,1′-binaphthyl-6,6′-diyl Moieties

, , , , &
Pages 4158-4170 | Received 12 Nov 2008, Published online: 29 Oct 2009
 

Abstract

Optically active aromatic ether ketone macrocycles containing 2,2′-dimethoxy-1,1′-binaphthyl-6,6′-diyl moieties were synthesized through electrophilic aromatic substitution reaction and stepwise nucleophilic aromatic substitution reactions. Structures of the resulting macrocycles were confirmed by NMR and matrix assisted laser desorption/ionization time of flight (MALDI-TOF) mass measurements.

ACKNOWLEDGMENT

This work was supported by a Grant-in-Aid for Young Scientists (B) (No. 20750173) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

Notes

a Reaction procedure: A DMF solution (12 mL) of diol 4a–c (0.5 mmol) was added dropwise over 6 h to a DMF solution (1.5 mL) of binaphthyl 3 (3 mmol) in the presence of K2CO3 (1.5 mmol) in N2 atmosphere. The reaction mixture was further stirred at 150°C for 24 h.

b Isolated yield.

a Reaction conditions: Binaphthyl 5a–c, 0.1 mmol; diol 4a–c, 0.1 mmol; K2CO3, 0.3 mmol; 150°C; N2 atmosphere.

a Measured in CHCl3 (5.0 × 10−5 mol/L).

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