KEY your name Chem 634 Problem Set 1 due Monday February 16 2004 Prof Fox Literature references are required only for steps 1 and 2 1 Outline a synthesis from commercial materials Provide a literature reference for each step 20 pts O O 1 pyrrolidine O O 2 H O LiAlH4 OH OH MnO2 O HO 2 Outline a synthesis Provide a literature reference for each step O Ph 1 LDA 2 BuI 1 LiAlH 4 2 H 3PO4 O O Pd 0 Bu Bu Ph PhBr K3PO4 3 Predict the products a 10 pts CH3 mCPBA CH3 CH3 OAc O 10 pts b H Li H OH H O H 4 Provide a mechanism 10 pts Cy N C N Cy OH O DMSO H3PO4 H Cy N C N Cy Me2S Any reasonable mechanism accepted Cy BuOH Me N S O NHCy Me H2C O S H N Cy O NHCy H CH2 Me O Me2S O S O Me 5 Rationalize the following observation O cat R2AlCl 20 pts OH OH OH 20 min 86 7 3h 95 5 7 unreacted ketone Initially the MPV reduction is under kinetic control transfer of hydride from the bulky aluminum reagent occurs from the equatorial face Me Me H O H3C O AlR2 H H3C O AlR2 However MPV reduction is reversible Oppenauer oxidation and the equilibrium favors the formation of the thermodynamically favoredtrans 2 methylcyclohexanol
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