Helical primary structures of 1,2-spiroannelated five-membered rings: attempted synthesis of (±)-tetraspiro[4.0.0.0.4.3.3.3]heneicosane

Tetrahedron - Tập 64 - Trang 4304-4312 - 2008
Tien Widjaja1, Lutz Fitjer1, Kathrin Meindl2, Regine Herbst-Irmer2
1Institut für Organische und Biomolekulare Chemie der Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
2Institut für Anorganische Chemie der Universität Göttingen, Tammannstrasse 4, D-37077 Göttingen, Germany

Tài liệu tham khảo

Gaini-Rahimi, 1999, Tetrahedron, 55, 3905, 10.1016/S0040-4020(99)00098-8 de Meijere, 1999, Angew. Chem., 111, 3682, 10.1002/(SICI)1521-3757(19991203)111:23<3682::AID-ANGE3682>3.0.CO;2-X 1999, Angew. Chem., Int. Ed., 38, 3474, 10.1002/(SICI)1521-3773(19991203)38:23<3474::AID-ANIE3474>3.0.CO;2-6 de Meijere, 2002, Chem.—Eur. J., 828, 10.1002/1521-3765(20020215)8:4<828::AID-CHEM828>3.0.CO;2-Y Fitjer, 2003, Tetrahedron, 59, 4443, 10.1016/S0040-4020(03)00617-3 Fitjer, 2004, Tetrahedron, 60, 1205, 10.1016/j.tet.2003.11.081 de Meijere, 2004, Angew. Chem., 116, 6715, 10.1002/ange.200461166 2004, Angew. Chem., Int. Ed., 43, 6553, 10.1002/anie.200461166 de Meijere, 2006, Chem.—Eur. J., 5697, 10.1002/chem.200600111 Widjaja, 2007, J. Org. Chem., 72, 9264, 10.1021/jo7017558 Wang, 2003, Synlett, 1497 Chamberlin, 1990, Org. React., 39, 1 Neumann, 1978, Chem. Ber., 111, 2785, 10.1002/cber.19781110807 Imamoto, 1989, J. Am. Chem. Soc., 111, 4392, 10.1021/ja00194a037 Tu, 2000, J. Chem. Soc., Perkin Trans. 1, 3791, 10.1039/b006182o Snape, 2007, J. Chem. Soc. Rev., 36, 1823, 10.1039/b709634h Weiser, 1997, J. Comput. Chem., 18, 1264, 10.1002/(SICI)1096-987X(19970730)18:10<1264::AID-JCC2>3.0.CO;2-L Allinger, 1989, J. Am. Chem. Soc., 111, 8551, 10.1021/ja00205a001 Tu, 1998, Chem. Lett., 285, 10.1246/cl.1998.285 Tu, 1999, J. Org. Chem., 64, 629, 10.1021/jo981097z Suemune, 1994, J. Chem. Soc., Perkin Trans. 1, 3441, 10.1039/p19940003441 Chan, 1995, Tetrahedron: Asymmetry, 6, 2953, 10.1016/0957-4166(95)00392-4 Bensimon, 1973, C.R. Acad. Sci. Paris, 276, 683 With the structurally related but sterically less demanding 2-(4-chlorobutyl)-cyclopentanone and 2-(4-bromobutyl)-cyclopentanone exclusive spiroalkylations have been observed: Eilerman, 1981, J. Chem. Soc., Chem. Commun., 30, 10.1039/C39810000030 Meyer, 1958, Chem. Ber., 91, 1616, 10.1002/cber.19580910809 Christol, 1959, Bull. Soc. Chim. Fr., 543 Krapcho, 1962, J. Am. Chem. Soc., 84, 1036, 10.1021/ja00865a033 Krapcho, 1965, J. Org. Chem., 30, 641, 10.1021/jo01013a503 Tsunoda, 1983, Tetrahedron Lett., 24, 83, 10.1016/S0040-4039(00)81333-7 Hutchins, 1972, J. Org. Chem., 37, 4190, 10.1021/jo00798a052 Carruthers, 1977, J. Chem. Soc., Perkin Trans. 1, 2411, 10.1039/P19770002411 Gerlach, 1972, J. Chem. Soc., Chem. Commun., 1215, 10.1039/C39720001215 Paquette, 1983, J. Am. Chem. Soc., 105, 7352, 10.1021/ja00363a024 Corey, 1975, Tetrahedron Lett., 2647, 10.1016/S0040-4039(00)75204-X Sheldrick, 2008, Acta Crystallogr., Sect. B, 64, 112, 10.1107/S0108767307043930