Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

TETRAHEDRON

卷:66

Article

Wenderski, Todd A.¹  Hoarau, Christophe¹  Mejorado, Lupe¹  Pettus, Thomas R. R.¹ 

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

关键词: Dearomatization;    Cyclohexadienone;    Hypervalent iodine;    Lactone;    Vinylogous ester;   

DOI  :  10.1016/j.tet.2010.05.041

来源: Elsevier

【 摘 要 】

The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.

【 授权许可】

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