Advances in Photochemistry by Noyes W

By Noyes W

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Chem. 15, 1065 (1976); and lit. cited therein 63. , Prentice Hall 1969 64. a) Niitzel, K. : in Houben-Weyl-MiJller, Methoden der Organischen Chemie, Vol. t3/2a, p. : in Houben-Weyl-Miiller, Methoden der Organischen Chemie, Vol. 13/I, p. 87, Stuttgart 1970 65. a) Kharasch, M. , Cooper, J. : J. Org. Chem. 10, 46 (1945); b) Vaskan, R. N. : Zh. Org. Khim. 11, 1818 (1975) 66. Reetz, M. , Westermann, J. : unpublished results, Univ. Bonn 1980 67. Niatzel, K. : in Houben-Weyl-M/Jller, Methoden der Organischen Chemie, Vol.

Although other ligands at titanium have not yet been tested, the results again demonstrate the principle of variable adjustment of carbanion selectivity by conversion into titanium reagents 21). Finally, a-deprotonated acyl silanes los) can be titanated with chlorotitanium triisophenoxide to form the corresponding titanium enolates which react erythro-selectively with aldehydes 14s). For example, the mixture of Z- and E-enolates derived from ethyl trimethylsilyl 49 Manfred T. Reetz ketone adds to benzaldehyde to afford a 92:8 mixture o f erythro and threo adducts.

This means that there is no simple way to prepare erythro aldols from cyclic ketones, since the enolates are geometrically fixed in the E geometry. We have prepared a number of titanium enolates by quenching the lithium analogs with chlorotitanium triisopropoxide 3, chloro- or bromotitanium tris(diethylamide) 15 or chlorotitanium tris(dimethylamide) 103 2s). In mqst cases the solutions can be freed from the ether or T H F and the stable liquid titanium enolates studied by N M R if so desired. In case of the amino derivative 186 flash distillation is possible.

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