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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Catalytic Asymmetric Allylation of 3,4-Dihydroisoquinolines and Its Application to the Synthesis of Isoquinoline Alkaloids. -An improved method allows formation of the 1-allylated tetrahydroisoquinolines (S)-and (R)-(III) with good enantioselectivity. These products can smoothly be converted into homolaudanosine (IV), crispine A (V), and the precursor (VI) of schulzeine A. -(MIYAZAKI, M.; ANDO, N.; SUGAI, K.; SEITO, Y.; FUKUOKA, H.; KANEMITSU, T.; NAGATA, K.; ODANAKA, Y.; NAKAMURA, K. T.; ITOH*, T.; J. Org. Chem. 76 (2011) 2, 534-542, http://dx.
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