Lecture 25 Mannich Reaction

Lecture 25 Mannich Reaction - O H N CH H H H 2 N CH 3 cat H...

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Unformatted text preview: O H N CH H H H 2 N CH 3 cat H + N H 3 C N H H H A B C D H H H 3 C N CH 3 H 3 C N OH H 3 C H N O Formaldehyde Mannich Reaction Primary or secondary amine or aldehyde that wont form enol Any carbonyl that forms enol O O + + H 2 NR H + H + N R H N R H R 1 H O H R 1 H O H R 1 H O enol N H R O H N H R HO N H R H 2 O N R R 1 H R 1 H imine R 1 H HO N H R 1 H H 2 O N H R H O H H Mannich Reaction R 1 H N N R O H R 1 O O H + amine and aldehyde form imine followed by reaction with enol R 1 H + H 2 NR + O Two mechanisms H H + O H R 1 O enol reacts with aldehyde followed by conjugate addition OH O O E1 H H 2 NR of amine to the enal R 1 R 1- H 2 O N R O H R 1 Conjugate addition O Mannich Reaction O O + H 2 N + H H O H + O N H O H + N H H H Predict the Product O O O N N N H N H N A B C D E How else could we make the same product? O N H L O Li O LDA H H O O O H + O heat H N H 2 N O OH O N H 2 OH N H O N H Challenge Problem Exam 2 in Spring 2008 Challenge Problem Exam 2 in Spring 2008 NaHCO 3 is a base and will deprotonate R-NH...
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Lecture 25 Mannich Reaction - O H N CH H H H 2 N CH 3 cat H...

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