General Entry to Asymmetric One-Pot [N + 2 + n] Cyclization for the Synthesis of Three- to Seven-Membered Azacycloalkanes

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• 作者：Shingo Harada ; Takeo Sakai ; Kiyosei Takasu ; Ken-ichi Yamada ; Yasutomo Yamamoto ; Kiyoshi Tomioka
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：September 7, 2012
• 年：2012
• 卷：77
• 期：17
• 页码：7212-7222
• 全文大小：513K
• 年卷期：v.77,no.17(September 7, 2012)
• ISSN：1520-6904

文摘

Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolate with 伪,蠅-dihaloalkane and N-alkylation. Isomerization of cis-azaheterocycles with a base yielded the trans-product, constituting a one-pot synthesis of cis-azacycles and a two-step synthesis of trans-azacycles. The four-step asymmetric synthesis of nemonapride highlights the general utility of the method.