School of Pharmacy, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
J Org Chem. 2011 Jan 21;76(2):534-42. doi: 10.1021/jo101956m. Epub 2010 Dec 28.
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.
使用烯丙基三甲氧基硅烷-Cu 作为亲核试剂，在 DTBM-SEGPHOS 作为手性配体的存在下，对 3,4-二氢异喹啉进行催化不对称烯丙基化反应，以高收率和立体选择性得到相应的手性 1-烯丙基四氢异喹啉衍生物。所得的烯丙基加合物被应用于几种异喹啉生物碱如crispine A 和 homolaudanosine 的合成。该反应进一步用于合成 Schulzeine A 的异喹啉部分。
