Benzomorphans hydrogenation

Benzamido-cinnamic acid, 20, 38, 353 Benzofuran polymerization, 181 Benzoin condensation, 326 Benzomorphans, 37 Benzycinchoninium bromide, 334 Benzycinchoninium chloride, 334, 338 Bifiinctional catalysts, 328 Bifiinctional ketones, enantioselectivity, 66 BINAP allylation, 194 allylic alcohols, 46 axial chirality, 18 complex catalysts, 47 cyclic substrates, 115, 117 double hydrogenation, 72 Heck reaction, 191 hydrogen incorporation, 51 hydrogen shift, 100 hydrogenation, 18, 28, 57, 309 hydrosilylation, 126 inclusion complexes, oxides, 97 ligands, 19, 105 molecular structure, 50, 115 mono- and bis-complexes, 106 NMR spectra, 105 olefin isomerization, 96... 

An alternative cyclization via a 1-tetralone intermediate has been achieved by Inoue and May,(15) Scheme 4.5. The key intermediate (41) was prepared from frmercuric acetate gave a mixture of the three benzomorphans (42, 49% 43, 13% 44, 5%). Hydrogenation of 42 afforded 3,lla-dimethyl-8-methoxybenzomorphan (45). 

Hitamura M, Hsiao Y, Noyori R, Takaya H. General asymmetric synthesis of benzomorphans and morphinans via enantioselective hydrogenation. Tetrahedron Lett. 1987 28 (41) 4829 832. 

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