Abstract
Using enantiomerically pure benzothiazines as templates, enantiomerically pure cyclobutanes were prepared. Such compounds are potentially interesting synthetic intermediates. The sequence developed for the preparation of these compounds, as well as some of their chemistry, is described.
Key words
benzothiazines - enantiomerically pure - cyclobutanes - stereoselective - metalation
References
1 Lee-Ruff E.
Mladenova G.
Chem. Rev.
2003,
103:
1449
2 Avenoza A.
Org. Lett.
2005,
7:
3597
3 Inanaga K.
Takasu K.
Ihara K.
J. Am. Chem. Soc.
2005,
127:
3668
4 Sarkar N.
Nayek A.
Ghosh S.
Org. Lett.
2004,
6:
1903
5 Jiménez-Osés G.
Corzana F.
Busto JH.
Pérez-Fernández M.
Peregrina JM.
Avenoza A.
J. Org. Chem.
2006,
71:
1869
6a Harmata M.
Hong X.
Org. Lett.
2004,
6:
2201
6b Harmata M.
Hong X.
Org. Lett.
2005,
7:
3581
7 Harmata M.
Hong X.
J. Am. Chem. Soc.
2003,
125:
5754
8a Rajender A.
Gais H.-J.
Org. Lett.
2007,
9:
579
8b Bosshammer S.
Gais H.-J.
Synthesis
1998,
919
8c Muller JFK.
Neuburger M.
Zehnder M.
Helv. Chim. Acta
1997,
80:
2182
8d Harmata M.
Tetrahedron Lett.
1988,
29:
5229
9 Crystallographic data (excluding structure factors) for some structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 658446 (5e ), 658447 (5g ), 672249 (6a ), 658448 (6c ), 658567 (6e ), 658449 (7 ), and 658450 (sulfone of 7 ). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
