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Synfacts 2011(8): 0923-0923  
DOI: 10.1055/s-0030-1260713
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral MOF for Carbonyl-Ene and Hetero-Diels-Alder Reactions

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Yoshinari Yuyama
K. S. Jeong, Y. B. Go, S. M. Shin, S. J. Lee, J. Kim, O. M. Yaghi, N. Jeong*
Korea University and Soongsil University, Seoul, Korea and University of California, Los Angeles, USA
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

A chiral metal-organic framework (MOF), (S)-KUMOF-1, was prepared from Cu(NO3)2 ˙3H2O and (S)-1H2 (1 = 2,2′-dihydroxy-6,6′-dimethylbiphenyl-4,4′-dicarboxylate). The carbonyl-ene reaction of 3,3,7-trimethyl-6-octenal was performed with Zn(II)/(S)-KUMOF-1 (9 mol equiv of Zn) to give the cyclic alcohol 2 in 92% yield with 50% ee. The hetero-Diels-Alder reaction was carried out with Ti/(S)-KUMOF-1 (0.95 mol equiv Ti) to give the cyclic ether 3 in 80% yield with 55% ee.