Introductiontoprotectinggroups - Introduction to protecting...

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1. What are protecting groups? Protecting groups are functional group modifications that can be used to shield, or protect functional groups against incompatible reagents or reactions. For example, the reaction below is impossible because the alcohol is sufficiently acidic to react with a Grignard reagent. If the alcohol is first protected, or masked somehow, the reaction can then be accomplished. OH Br Mg X OH MgBr H + O Br Mg OtBu MgBr 2. What are the requirements for protecting groups? 1) It should be easy to put on 2) It should be stable to subsequent reactions 3) It should be easy to take off under highly specific conditions that do not affect the rest of the molecule Also desirable… 1) It should be easy to characterize and avoid introduction of stereogenic centers 2) It should not make purification harder (and perhaps make it easier?) 3) Removal of the protecting group should not lead to a separation problem Example: HO ? HO
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This note was uploaded on 07/02/2011 for the course CHEM S341 taught by Professor Staff during the Spring '11 term at Indiana.

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Introductiontoprotectinggroups - Introduction to protecting...

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