Tetrahedron letters

General asymmetric synthesis of benzomorphans and morphinans via enantioselective hydrogenation

M Kitamura, Y Hsiao, R Noyori, H Takaya

文献索引：Kitamura, M.; Hsiao, Yi; Noyori, R.; Takaya, H. Tetrahedron Letters, 1987 , vol. 28, # 41 p. 4829 - 4832

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被引用次数: 91

摘要

The hydrochloride of 4a was prepared as follows. Reduction of tiglic acid (LiAlH4, ether, 0–40 °C) gave (E)-2-methyl-2-buten-1-ol (bp 65–7O°C/76 mmHg, 85% yield), whose bromination (PBr 3 , 0 °C, 91% yield) followed by cyanation (CuCN, DMF, 26 °C, 76% yield) furnished ( E )-3-methyl-3-pentenenitrile. Reduction (LiAlH 4 + AlCl 3 , ether, 0–26 °C) of the cyanide gave ( E )-3-methyl-3-pentenylamine (bp 35–40 °C/25 mmHg). N-(3′-Methyl-3′-pentenyl)-4- ...