Chem634_F11_PS06 - Chemistry 634 Advanced Organic Chemistry...

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Chemistry 634: Advanced Organic Chemistry – Synthesis and Reactivity Fall 2011, University of Delaware Prof. Donald Watson Problem Set 8, 30 points Due Beginning of Class 12/06/11 You may work in groups, unless otherwise noted. Do not try to fit answers on these pages, use separate paper. 1) Provide the missing reagents. Note more than one step may be needed. R R OH t-Bu O t-Bu O OTBS R R OH R R OH R R O OMe R O R Bu R O R Me Me Me Me R R OH OH this enant. only R R O R OH R Ph O R O R Et R O R CO 2 Me R R Ph R Bu OTBS R Ph CO 2 Me CO 2 Me Bu R R Me Me
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2) a) In class, we have discussed that Lewis acids can promote the formation of oxo-carbenium ions and trigger the addition of allyl silanes to them. Sometimes the oxo-carbenium ion can form from a suitably protected alcohol and an aldehyde. Given that major hint, rationalize the following transformation including the stereochemical outcome (DO NOT LOOK UP THE ANSWER TO THIS). Me
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Chem634_F11_PS06 - Chemistry 634 Advanced Organic Chemistry...

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