1-Bromo-2-ethoxycyclopropyllithium: A Synthetic Equivalent of 2-Lithio-or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and …

Y Morizawa, A Kanakura, H Yamamoto…

Index: Morizawa, Yoshitomi; Kanakura, Akihiro; Yamamoto, Hajime; Hiyama, Tamejiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 7 p. 1935 - 1942

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Citation Number: 21

Abstract

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at− 95° C in tetrahydrofuran. The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields. The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives. The reaction ...