1
α-Carbonyl Nucleophiles
Michael and Stork reactions Aldol condensation
Claisen condensation
The Michael Reaction
Addition of any β-dicarbonyl compound to any α,β-unsaturated carbonyl compound, in the β position.
Disampaikan oleh : Dr. Sri Handayani 2013
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2 The Michael Reaction
Addition of any β-dicarbonyl compound to any α,β-unsaturated carbonyl compound, in the β position.
Generic “Michael” addition
3 Mechanism of the Michael
Reaction
The Stork Enamine Reaction
O O
CH2CH2CH O
a.
b.
c. H+/H2O
N H
CH2 CH CH
4 Mechanism of the Stork
Enamine Reaction
5 The Aldol addition and its
products
6 The Aldol condensation makes
α,β-unsaturated carbonyls
7 What’s the mechanism?
8 Mixed Aldol works if one has
no α-hydrogens
9 The Claisen condensation
makes β-keto esters
10 The essential difference
between Aldol and Claisen
leaving group
11
Mixed Claisen in which one component has no α-hydrogens
Mixed Claisen
between ketone and ester
Why don’t we get Aldol with ester enolate nucleophile?
12
Mixed Claisen with formic or carbonate ester
13 Solution
14 Solution
16 Intramolecular Aldol can give
two possible ring sizes
17 Six-membered rings
18 The Robinson Annulation: Michael Addition,
19 Retrosynthetic breakdown
20 Retrosynthetic breakdown
