UNIT 5 - Enolates-01-aldol robinson

UNIT 5 - Enolates-01-aldol robinson - SC6POC OMalley...

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SC6POC – O’Malley Enolates 1 Name: ______________________ 1003-7, 1013-14, 1017-27, 1046 (alkylation, aldol, Robinson) © S. O’Malley 2010 1. Enolate formation / alkylation O LDA Br O O 2. Enolate alkylation (beta-ketoesters and diesters)and saponification / decarboxylation O OEt O 1. NaOEt 2. Br O OEt O O OH O O -ketoester i. NaOH ii. H 3 O + 3. Enolate conjugate addition (Michael addition) EtO O O EtO O O NaOEt EtOH OEt O CO 2 Et 4. Aldol addition / condensation O + H O OH - H 2 O O OH O OH -
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5. Robinson annulation (Michael addition followed by aldol condensation)
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UNIT 5 - Enolates-01-aldol robinson - SC6POC OMalley...

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