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Volumn 49, Issue 12, 2010, Pages 2175-2177

Enantioselective kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine (iii) species

Author keywords

Asymmetric oxidation; Hypervalent compounds; Iodine; Organocatalysis; Spirolactones.

Indexed keywords

ASYMMETRIC OXIDATION; CHEMICAL EQUATIONS; CHIRAL CATALYST; ENANTIOSELECTIVE; HYDROGEN BONDING INTERACTIONS; HYPERVALENT COMPOUNDS; HYPERVALENT IODINE; IN-SITU; IODOSYLARENE; ORGANOCATALYSIS; RATIONAL DESIGN;

EID: 77949413500     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907352     Document Type: Article
Times cited : (404)

References (29)
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    • d) up to 72% ee: H. Tohma, S. Takizawa, H. Watanabe, Y. Fukuoka, T. Maegawa, Y. Kita, J. Org. Chem. 1999, 64, 3519;
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    • b) up to 29% ee: see Ref. [2h].
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    • We do not yet have any experimental evidence for the nonbonding interactions between the iodine(III) center and functional groups in 6. However, there are many reports on the intraor intermolecular secondary interactions of IIII and Iv. For selected examples, see: a) V. V. Zhdankin, A. E. Koposov, J. T. Smart, J. Am. Chem. Soc. 2001, 123, 4095;
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    • -7 was easily prepared from resorcinol, see: S. Tsujiyama, K. Suzuki, D. B. Guthrie, H. M. Gibney, D. P. Curran, Org. Synth. 2007, 84, 272.
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    • For details, see the Supporting Information
    • For details, see the Supporting Information.
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    • We also examined the spirolactonization reactions of simple phenol derivatives. Unfortunately, no sufficient results were observed under our present conditions. The desired spirolactones were obtained in very low yield <5, as well as dimerization products and other side-products
    • We also examined the spirolactonization reactions of simple phenol derivatives. Unfortunately, no sufficient results were observed under our present conditions. The desired spirolactones were obtained in very low yield (<5%) as well as dimerization products and other side-products.


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