Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 2, Pages 534-542Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101956m
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Funding
- MEXT (Ministry of Education, Culture, Sports, Science and Technology)
- Japan Society for the Promotion of Science
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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.
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