First synthesis and stereochemistry of enantiomerically pure spiroselenurane and spirotellurane using the 2-exo-hydroxy-10-bornyl group as a chiral ligand

作者: Jian Zhang , Shigemasa Takahashi , Shinichi Saito , Toru Koizumi

DOI: 10.1016/S0957-4166(98)00352-8

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摘要: Abstract The first synthesis of enantiomerically pure spiroselenuranes 8a–d and spirotelluranes 12a,b, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been developed proceeds in good yield with excellent diastereoselectivity. X-ray analysis spirotellurane 12a indicated that spirochalcogenuranes have trigonal bipyramidal (TBP) structure around chalcogenium atom. A comparison spectroscopic properties is also discussed.

参考文章(39)
J. C. Martin, E. F. Perozzi, Isolable Oxysulfuranes in Organic Chemistry Science. ,vol. 191, pp. 154- 159 ,(1976) , 10.1126/SCIENCE.191.4223.154
I. Kapovits, A. Kálmán, Formation and structure of a four-co-ordinate organo-sulphur(IV) compound J. Chem. Soc. D. ,vol. 0, pp. 649b- 650 ,(1971) , 10.1039/C2971000649B
J. Tércio B. Ferreira, Alfredo R. M. De Oliveira, João V. Comasseto, A Convenient Method of Synthesis of Dialkyltellurides and Dialkylditellurides Synthetic Communications. ,vol. 19, pp. 239- 244 ,(1989) , 10.1080/00397918908050975
Karen L. House, R. Bruce Dunlap, Jerome D. Odom, Zhen Ping Wu, Donald Hilvert, Structural characterization of selenosubtilisin by selenium-77 NMR spectroscopy Journal of the American Chemical Society. ,vol. 114, pp. 8573- 8579 ,(1992) , 10.1021/JA00048A033
Jian Zhang, Shinichi Saito, Toru Koizumi, Acidic and basic hydrolysis of an optically pure spiro-lambda(4)-sulfurane: Completely opposite stereochemical outcome Journal of the American Chemical Society. ,vol. 120, pp. 1631- 1632 ,(1998) , 10.1021/JA973039L
Tamiko Takahashi, Noriyuki Kurose, Saburo Kawanami, Yoshitsugu Arai, Toru Koizumi, Motoo Shiro, Optically pure haloselenuranes. First synthesis and nucleophilic substitutions Journal of Organic Chemistry. ,vol. 59, pp. 3262- 3264 ,(1994) , 10.1021/JO00091A008
Hans J. Reich, Organoselenium stereochemistry. Configurational stability of dialkoxydiarylselenium compounds Journal of the American Chemical Society. ,vol. 95, pp. 964- 966 ,(1973) , 10.1021/JA00784A077
Björn Lindgren, J.-L. Fiasson, S. Liaaen-Jensen, K. J. Watson, Sigfrid Svensson, Synthesis and Partial Resolution of 7-Carboxy-3,3'-spirobi(3-selenaphthalide). Acta Chemica Scandinavica. ,vol. 26, pp. 2560- 2561 ,(1972) , 10.3891/ACTA.CHEM.SCAND.26-2560
Tibor Ádám, Ferenc Ruff, István Kapovits, Dénes Szabó, Árpád Kucsman, Diarylbis(acylamino)spiro-λ4-sulfanes and cyclic acylaminosulfonium salts. A kinetic study of equilibrium and hydrolysis reactions Journal of The Chemical Society-perkin Transactions 1. pp. 1269- 1276 ,(1998) , 10.1039/A705660E
William Y. Lam, Eileen N. Duesler, J. C. Martin, A comparison of hypervalent bond polarizabilities in sulfuranes (10-S-4 species) and persulfuranes (12-S-6 species) Journal of the American Chemical Society. ,vol. 103, pp. 127- 135 ,(1981) , 10.1021/JA00391A024