1. Enantioselective deprotonation reactions of (arene)tricarbonylchromium complexes, and 2. Reductive lithiation of (arene)tricarbonylchromium acetals.
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Chemistry and Biochemistry
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Chapter 1. Chiral alkyllithium bases are able to selectively lithiate either the pro R or pro S ortho site of several monosubstituted $\eta\sp6$-(arene)tricarbonylchromium (0) complexes. The chiral alkyllithium bases were prepared from the corresponding chloride using the radical anion, lithium 4,4$\sp\prime$-di(tert-butyl)biphenyl (LiDBB). The base derived from 8-phenylmenthol provided the highest degree of asymmetric induction in $\lbrack\eta\sp6$-(dimethoxymethyl)benzene) tricarbonylchromium (0) with a respectable chemical yield. Chapter 2. $\eta\sp6$-(Arene)tricarbonylchromium (0) acetal complexes can be reduced at low temperatures by the radical anion, LiDBB, to generate the corresponding benzyllithium complexes. Once formed, these benzyllithium complexes can trap a variety of electrophiles to give benzyl-functionalized chromium complexes in good yields. In addition, the reduction of an ortho substituted complex, and subsequent trapping with an electrophile occurs with a high degree of diastereoselectivity. Source: Masters Abstracts International, Volume: 34-06, page: 2379. Adviser: J. R. Green. Thesis (M.Sc.)--University of Windsor (Canada), 1996.
Siwek, Michael John., "1. Enantioselective deprotonation reactions of (arene)tricarbonylchromium complexes, and 2. Reductive lithiation of (arene)tricarbonylchromium acetals." (1996). Electronic Theses and Dissertations. 509.