Asymmetric synthesis of 1-aryl-1,2-ethanediols from arylacetylenes by palladium-catalyzed asymmetric hydrosilylation as a key step.
作者： Toyoshi Shimada , Kotaro Mukaide , Akihiro Shinohara , Jin Wook Han , Tamio Hayashi
DOI: 10.1021/JA017617G
关键词:
摘要: Double hydrosilylation of arylacetylenes with trichlorosilane catalyzed first by platinum and second a chiral monophosphine−palladium complex generated the corresponding 1,2-bis(silyl)-1-arylethanes, oxidation which hydrogen peroxide gave 1-aryl-1,2-diols high enantiomeric purity (94−98% ee) in yields.
acs.org
sci-hub.se 参考文章(8)
Tsutomu Katsuki, K. Barry Sharpless, First practical method for asymmetric epoxidation Journal of the American Chemical Society. ,vol. 102, pp. 5974- 5976 ,(1981) , 10.1021/JA00538A077
Paul Busse, Milton Orchin, A new general synthesis of Zeise's dimer, [PtCl2(C2H4)]2, and its analogs Journal of Organometallic Chemistry. ,vol. 128, pp. 85- 87 ,(1977) , 10.1016/S0022-328X(00)92037-0
Steven G. Hentges, K. Barry Sharpless, Asymmetric induction in the reaction of osmium tetroxide with olefins Journal of the American Chemical Society. ,vol. 102, pp. 4263- 4265 ,(1980) , 10.1021/JA00532A050
Kohei Tamao, Junichi Yoshida, Hiraku Yamamoto, Toshio Kakui, Hiroshi Matsumoto, Masatada Takahashi, Atsushi Kurita, Masao Murata, Makoto Kumada, Organofluorosilicates in organic synthesis. 12. Preparation of organopentafluorosilicates and their cleavage reactions by halogens and N-bromosuccinimide. Synthetic and mechanistic aspects Organometallics. ,vol. 13, pp. 355- 368 ,(1982) , 10.1021/OM00062A022
Tamio Hayashi, Seiji Hirate, Kenji Kitayama, Hayato Tsuji, Akira Torii, Yasuhiro Uozumi, Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes: Ligand Modification and Mechanistic Studies Journal of Organic Chemistry. ,vol. 66, pp. 1441- 1449 ,(2001) , 10.1021/JO001614P
Herbert C. Brown, George Zweifel, Hydroboration. XI. The Hydroboration of Acetylenes—A Convenient Conversion of Internal Acetylenes into cis-Olefins and of Terminal Acetylenes into Aldehydes Journal of the American Chemical Society. ,vol. 83, pp. 3834- 3840 ,(1961) , 10.1021/JA01479A024
Heinrich Becker, S. Bruce King, Masahiko Taniguchi, Koenraad P. M. Vanhessche, K. Barry Sharpless, New Ligands and Improved Enantioselectivities for the Asymmetric Dihydroxylation of Olefins Journal of Organic Chemistry. ,vol. 60, pp. 3940- 3941 ,(1995) , 10.1021/JO00118A005
Tamio Hayashi, Chiral monodentate phosphine ligand MOP for transition-metal-catalyzed asymmetric reactions. Accounts of Chemical Research. ,vol. 33, pp. 354- 362 ,(2000) , 10.1021/AR990080F