Preparation of Methoxy-Substituted Optically Active 7-Alkoxycarbonylcycloheptatrienes and Their Acid-Promoted Rearrangements

Takashi Sugimura; Masami Kagawa; Naoko Ohuchi; Kazutake Hagiya; Tadashi Okuyama

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Preparation of Methoxy-Substituted Optically Active 7-Alkoxycarbonylcycloheptatrienes and Their Acid-Promoted Rearrangements

机译：甲氧基取代的光学活性7-烷氧基羰基环庚烯的制备及其酸促进的重排

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Four optically active cycloheptatriene derivatives carrying a methoxy group(s) at different positions were prepared by the 2,4-pentanediol-tethered Buchner reaction.In addition to the high stereoselectivity,the tether also controlled the regioselectivity in a good-to-high degree.Some of the products are unstable under acidic conditions,resulting in isomerization through a prototropic reaction or aromatization.The Br0nsted acid promoted prototropic isomerization by regio-and stereoselective protonation and ensuing deprotonation,while the Lewis acid-catalyzed reaction provided an aromatized product via the norcaradiene tautomer.

机译：通过2,4-戊二醇束缚的布赫纳反应制备了四个在不同位置带有甲氧基的旋光环庚三烯衍生物。除具有高的立体选择性外，该束缚剂还可以从高到高的程度控制区域选择性。一些产品在酸性条件下不稳定，导致通过质子反应或芳构化进行异构化。布朗斯台德酸通过区域和立体选择性质子化并随后去质子化促进质子异构化，而路易斯酸催化的反应则通过降冰片烯互变异构体。

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《Bulletin of the Chemical Society of Japan》 |2005年第4期|共6页
作者
Takashi Sugimura; Masami Kagawa; Naoko Ohuchi; Kazutake Hagiya; Tadashi Okuyama;
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1. Preparation of Methoxy-Substituted Optically Active 7-Alkoxycarbonylcycloheptatrienes and Their Acid-Promoted Rearrangements [J] . Takashi Sugimura, Masami Kagawa, Naoko Ohuchi, Bulletin of the Chemical Society of Japan . 2005,第4期

机译：甲氧基取代的光学活性7-烷氧基羰基环庚烯的制备及其酸促进的重排
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Preparation of Methoxy-Substituted Optically Active 7-Alkoxycarbonylcycloheptatrienes and Their Acid-Promoted Rearrangements

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