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Synfacts 2015; 11(1): 0054
DOI: 10.1055/s-0034-1379747
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chiral Furans via Asymmetric [3+2] Cycloaddition

Contributor(s):
Hisashi Yamamoto
,
Sukalyan Bhadra
Chen W, Fu X, Lin L, Yuan X, Luo W, Feng J, Liu X, Feng X * Sichuan University, Chengdu, P. R. of China
An Asymmetric [3+2] Cycloaddition of Alkynes with Oxiranes by Selective C–C Bond Cleavage of Epoxides: Highly Efficient Synthesis of Chiral Furan Derivatives.

Chem. Commun. 2014;
50: 11480-11483
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

asymmetric [3+2] cycloaddition - epoxides - furans - nickel

Significance

Tetrahydrofurans and 2,5-dihydrofurans containing a stereocenter are often found in natural products and medicinal compounds. Ni(ClO4)2·6H2O in the presence of an N,N′-dioxide ligand promotes the asymmetric [3+2] cycloaddition of alkynes with epoxides via a regioselective C–C bond cleavage to give 2,5-dihydrofurans. A catalytic amount of LiNTf2 was necessary to increase the yield of the cycloaddition process.


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Comment

Notably, the asymmetric [3+2] cyclo­addition of an alkene and an epoxide under optimized conditions afforded an optically active tetrahydrofuran derivative. According to the proposed activation model, the chiral nickel complex activates the epoxide to form a carbonyl ylide intermediate, through which the alkyne attacks from the re face, leading to the R-configured product.


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