assignment3 - CHM 3120 Assignment 3 1. Show the product of...

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1 CHM 3120 Assignment 3 1. Show the product of the following reactions. Draw intermediates to explain the observed stereochemistry: Ph O Et SMe Ph O Et SMe H O Et N EtMgBr TBDPSO CHO OTBS N OLi O O a) LiBH(sBu) 3 b) c) d) + Zn(BH 4 ) 2 2. Consider the following reaction: O Me O Me Ph OH 1) LDA 2) PhCHO a) What is the major enolate formed? b) Explain why this is the major enolate. c) Show the reaction pathways leading to the two diasteriomers formed. d) What is the stereochemistry of the major product (syn or anti)? Indicate on your reaction pathway the unfavorable interaction. 3. a) Show the reaction pathways leading to the two products of the following reaction: O O 1) LDA 2) H O b) Indicate the major product formed and show the unfavorable interaction disfavoring the minor product. 4. a) Show the reaction pathways leading to the two products of the following reaction: 1) LDA 2) H O O b) Indicate the major product formed and show the unfavorable interaction disfavoring the minor product.
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This note was uploaded on 12/11/2009 for the course CHM Chm3120 taught by Professor Olgilvie during the Spring '09 term at University of Ottawa.

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assignment3 - CHM 3120 Assignment 3 1. Show the product of...

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