Organic Chemistry

Application of spectroscopy of organic chemisttry by Brand, Eglinton

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By Brand, Eglinton

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Their comparatively low reactivity often generates the need for catalysis, providing a dimension of control which may be exploited to various stereochemical ends [ 13I. The application in this case was delightfully oblique (C-C bond formation is not usually employed to elaborate a protecting group in a synthetic intermediate), and nicely illustrated the versatility of these widely-used reagents. The progression from desymmetrisation (Scheme 2) to derdcemisation (Schemes 3-6) leads to a useful general insight.

Lnterestingly the product is 56. This suggests that the chirality transfer is - other than postulated by the authors - not analogous to the model for Mg12*4. The examples described here should give an impression of the numerous applications of oxazolines in organic synthesis. The easy accessibility combined with the excellent qualities in transferring chirality will surely lead to many more applications of oxazolines. Acknowledgement: The authors thank the Fonds der Chemischen Industrie for financial support.

F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851; T. Bach, Angew. Chem. 1994, 106,433; Angew. , Int. Ed. Engl. 1994, 33, 417. [I41 For a selection of methods applicable to diols, see H. Fujioka, Y. Nagatomi, N. Kotoku, H. Kitagawa, Y. Kita, Tetrahedron Lett. 1998, 39, 7309, and references therein. [IS] M. Kinugasa, T. Harada, A. Oku, J. Am. Chem. Soc. 1997, 119, 9067; M. Kinugasa, T. Harada, A. Oku, Tetrahedron Lett. 1998, 39, 4529. [I61 T. Harada, T. Nakamura, M. Kinugasa, A.

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