Asymmetric Synthesis of Tetrahydroquinolin-3-ols via CoCl2-Catalyzed Reductive Cyclization of Nitro Cyclic Sulfites with NaBH4.

[摘要]：Nonracemic 3-hydroxy-1,2,3,4-tetrahydroquinolines such as I (R = H, MeO, PhCH2O, BuCH2O; R1 = H, MeO, PhCH2O; RR1 = OCH2O) are prepd. chemoselectively by redn. of nitrophenyl cyclic sulfites such as nonracemic II (R = H, MeO, PhCH2O, BuCH2O; R1 = H, MeO, PhCH2O; RR1 = OCH2O) with sodium borohydride and cobalt (II) chloride. The nonracemic nitrophenyl-substituted cyclic sulfites are prepd. in two or three steps by asym. dihydroxylation of trans-cinnamates, chemo- and regioselective nitration of the arenes, and cyclic sulfite formation with thionyl chloride. I (R = R1 = MeO) and the enantiomer of I (R = R1 = H) are converted to intermediates for the prepn. of the anachelin H chromophore and for the dopamine D2 receptor antagonist PNU 95666 E, resp.

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