Catalytic Asymmetric Allylation of 3,4-Dihydroisoquinolines and Its Application to the Synthesis of Isoquinoline Alkaloids

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• 作者：Michiko Miyazaki ; Nami Ando ; Keita Sugai ; Yuki Seito ; Hiromi Fukuoka ; Takuya Kanemitsu ; Kazuhiro Nagata ; Yuki Odanaka ; Kazuo T. Nakamura ; Takashi Itoh
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：January 21, 2011
• 年：2011
• 卷：76
• 期：2
• 页码：534-542
• 全文大小：992K
• 年卷期：v.76,no.2(January 21, 2011)
• ISSN：1520-6904

文摘

A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A.