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Synfacts 2014; 10(7): 0730
DOI: 10.1055/s-0034-1378260
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Azahelicenes via Intramolecular Hydroarylation of Alkynes

Contributor(s):
Hisashi Yamamoto
,
Wafa Gati
Nakamura K, Furumi S, Takeuchi M, Shibuya T, Tanaka K * Tokyo University of Agriculture and Technology, Koganei, Japan Science and Technology Agency, Kawaguchi and National Institute for Materials Science, Tsukuba, Japan
Enantioselective Synthesis and Enhanced Circularly Polarized Luminescence of S-Shaped Double Azahelicenes.

J. Am. Chem. Soc. 2014;
136: 5555-5558
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Publication History

Publication Date:
16 June 2014 (online)

 
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Key words

asymmetric synthesis - azahelicenes - intramolecular hydroarylation - gold

Significance

The authors report an enantioselective synthesis of azahelicenes and S-shaped double azahelicenes, promoted by gold/silver triflate co-catalyzed intramolecular hydroarylation of alkynes. The photophysical properties of both azahelicenes and S-shaped double azahelicenes were then evaluated by measuring the circularly polarized luminescence activity.


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Comment

Azahelicenes and S-shaped double azahelicenes were successfully synthesized via catalytic enantioselective sequential hydroarylation of achiral diynes and tetraynes in high yields and moderate to high enantioselectivities. Interestingly, the chiroptical property of the S-shaped double azahelicenes is very promising, since the circularly polarized luminescence activity of double azahelicenes was amazingly much higher than that of the simple azahelicenes.


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