Chem 253 Problem Set 7 Due: Friday, December 3, 2004
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1 Chem 253 roblem Set 7 ue: Friday, ecember 3, 2004 Name TF. Starting with the provided starting material, provide a concise synthesis of. You may use any other reagents for your synthesis. It can be assumed that the desired enantiomer will be obtained from asymmetric transformations (knowledge of exact chrial ligand structure is not necessary). C 7.5 mol% N N C Boc 2 pyridine Boc mol% [d 2 (dba) 3 ]*CCl 3 C 2 Cl 2, 30 mol% Bu 4 NCl, 0 o C + Ac (.5 eq) SiMe 3 20 mol% (i-r) 3 25 mol% d(ac) 2 toluene, reflux, 2h Trost Chem. Eur. J. 2004, 0, 2237
2 2. Trost has developed a highly enantioselective and regioselective nucleophilic addition of alcohols to vinyl epoxides. Taking into account the observations below, propose a mechanism for this transformation and provide an explanation for the high regioselectivity observed. The stereochemical outcome of the reaction need not be justified. bservations: Less than 6% conversion is observed in the absence of triethylborane. Triethylborane does not react with the epoxide in the absence of a palladium catalyst. Triethylborane is rapidly converted to methoxydiethylborane under the reaction conditions. 3 C + C 3.0 equiv.0 equiv.0 mol% d 2 (dba) 3 CCl mol%.0 mol% (C 2 5 ) 3 B C 2 Cl 2, rt, 3 h 3 C C 3 88% yield 94% ee 2 N N 2 Answer d 2 (dba) 3 CCl 3 2 Ligand dba 3 C C 3 d 3 C C 3 3 C C 3 B2 B C 3 d dba C 3 B C 3 C 2 6 B + C 3 3 C d C 3 C 3 B Formation of a boronate complex stabilizes the alkoxide resulting from epoxide opening and directs methoxide attack at the more substituted carbon atom of the p-allyl complex. Trost, B. M.; McEachern, E. J.; Toste, F.. J. Am. Chem. Soc. 998, 20,
3 3. rovide a mechanism that accounts for the formation of all three products in this rhodium catalyzed oxidative cyclization. Note that there should be at least one common intermediate in the formation of all the products. Me 2 C Me 2 C 5 mol% [Cl(C)( 3 ) 2 ] 5 mol% AgSbF 6 atm C, TF, 40 o C, 23h Me 2 C Me 2 C Me 2 C Me 2 C 8% 25% Me 2 C Me 2 C Note that the ligands on the rhodium have been ommitted for clarity. 45% Me 2 C Me 2 C L n I Me 2 C Me 2 C I III C III III III C C insertion then reductive elimination C insertion then reductive elimination Me 2 C Me 2 C Me 2 C Me 2 C Me 2 C Me 2 C Wender ACIEE, 2003, 853
4 4. rovide two distinct mechanisms for the reductive cyclization of the,6-diyne shown below. Note that a rhodium monohydride species is the active catalyst (eq ). Which mechanism would you consider more likely to be operating and why? 3 mol% (C) 2 Tf 3 mol% rac-bina atm 2 85% yield 3 mol% (C) 2 Tf 3 mol% rac-bina atm 2 79% yield (C) 2 Tf + rac-bina 2 (rac-bina)tf 2 (rac-bina)() 2 Tf Tf (rac-bina) () 2 cyclooctane Mechanism : Answer: xidative cyclization mechanism (rac-bina) xidative Addition 2 (rac-bina) xidative Cyclization
5 4. rovide two distinct mechanisms for the reductive cyclization of the,6-diyne shown below. Note that a rhodium monohydride species is the active catalyst (eq ). Which mechanism would you consider more likely to be operating and why? 3 mol% (C) 2 Tf 3 mol% rac-bina atm 2 85% yield 3 mol% (C) 2 Tf 3 mol% rac-bina atm 2 79% yield (C) 2 Tf + rac-bina 2 (rac-bina)tf 2 (rac-bina)() 2 Tf Tf (rac-bina) () 2 cyclooctane Mechanism 2: Answer: Alkyne hydrometallation mechanism (rac-bina) xidative Addition 2 (rac-bina) Insertion Insertion The oxidative cyclization mechanism seems more likely since a very regioselective insertion would be required in order to obtain the observed diene as the sole product of the reaction. It should be noted that the favored mode of insertion into arylated alkynes is analogous to that observe for styrene derivaitves and opposite to that required for product formation. Jang,.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 26,
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