PS4Fa09ans - Advanced Organic Chemistry Synthesis CHEM...

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1 Advanced Organic Chemistry: Synthesis Name:___ Johnny Damon _______ CHEM 311/511 Problem Set #4 Due: Tuesday October 27, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete ten of the twelve boxes and graduate students must complete all twelve. (10 pts.) a) Ru Cl Cl O N N (40%) , BQ J. T. Njardson et al. Org. Lett. 2009, 11, 4492-5 b) O t-BuO 2 C STol CO 2 Et NO 2 O HO 2 C STol CO 2 Et NO 2 CF 3 CO 2 H Y. Hayashi et al. Angew. Chem. Int. Ed . 2009, 48, 1307. c) O O pTsOH HOCH 2 CH 2 OH O O O 1) Li, NH 3 , t-BuOH 2) NC-CO 2 Me O O O MeO 2 C H E. A. Theodorakis et al. JOC 2001, 66, 8843. d) N N O Ph H OBn H 2 , Pd(cat.) L. E. Overman et al. JACS 2008, 130, 11297. N N O Ph H OH
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