UNIT 5 - Enolates-06-mannich claisen

UNIT 5 - Enolates-06-mannich claisen - 2 H 3 O e Claisen O...

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SC6POC O’Malley Enolates 6 Name _______________________ Wade: 1015-1017, 1027-1042 (Claisen, Enamines, Mannich) © S. O’Malley 2010 1. Claisen condensation OEt O + OEt O 1. NaOEt, EtOH 2. H 3 O + O OEt O 2. Enamine formation O NH N cat H 3 O + 3. Enamine alkylation / hydrolysis N Br N O H 3 O + 4. Mannich Reaction (a MULTI-COMPONENT reaction!!) O + H O + NH 2 H + O HN + H 2 O aldehyde amine ketone -aminoketone
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PROBLEMS 1. Predict the products of the following reactions: a. Mannich NH O Me H O H H + b. Mannich O Ph Ph MeNH 2 2 H H O H + + c. Mannich HN O Me Ph H O H + d. similar to Claisen O H 3 CO O H 1. NaOMe
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Unformatted text preview: 2. H 3 O + e. Claisen O O O 1. NaOEt 2. H 3 O + f. Enolate alkylation, etc EtO O OEt O 1. xs NaOEt 2. 3. NaOH 4. H 3 O + , Br Br 2. Show what esters would undergo Claisen condensation to yield the following products: a. O O O b. O O O c. O CO 2 Me d. O Me O OEt 3. Show a mechanism for the following tandem enamine formation / conjugate addition / hydrolysis: Ph O 1. pyrrolidine H 3 O + 2. 3. H 3 O + Ph O Ph O Ph O...
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