PS2Fa09ans - Advanced Organic Chemistry Synthesis CHEM...

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Advanced Organic Chemistry: Synthesis Name:___ Bruce Springsteen _____ CHEM 311/511 Problem Set #2 Due: Tuesday, September 22, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete three of the four problems and graduate students must complete all four. (4 pts.) a) CHO O N O O Ph 1) Bu 2 BOTf, Et 3 N, CH 2 Cl 2 -78 o C to 0 o C 2) O N O O Ph OH D. R. Williams et al. Tet. Lett. 1997, 38, 6825 b) O O NaOH, H 2 O O J. E. McMurry et al. JACS 1971, 93, 5309 c) H O H H 1) LDA 2) CH 3 CHO 3) TsOH H O H H D. F. Taber et al. 1980, 102, 5085 d) O H OTIPS TIPSO OH + OSiMe 3 H OAc MgBr 2 . Et 2 O -20 to 4 o C O OH OAc TIPSO OH TIPSO D. W. C. MacMillan et al. Science 2004, 305, 1752 2. Answer the following questions about the recently reported alkylation reaction shown below. (6 pts.) (Qi-Xiang Guo et al. Org. Letters 2009 , ASAP, DOI: 10.1021/ol901892s)
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a) Identify the nucleophile (Nu) and the electrophile (E+) in the reaction. Nu= E+= b) Propose a mechanism for the reaction. You may ignore stereochemistry for the mechanism.
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PS2Fa09ans - Advanced Organic Chemistry Synthesis CHEM...

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