Published TCIMAIL newest issue No.197
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Diene Derivative with High Reactivity for Diels-Alder Reaction
trans-3-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-1,3-butadiene-1-amine (1), also known as Rawal’s diene,1) is a building block used in (hetero) Diels-Alder reactions. It has been reported that the reactivity of 1 is thousand times more when compared to Danishefsky-Kitahara diene because of higher HOMO level2) of 1 to that of Danishefsky-Kitahara diene. Additionally, the given silyl enol ether is hydrolyzed by acid to afford an α,β-unsaturated ketone. There have been many reports of the total syntheses of natural products using 1, which suggests the usefulness of this method.
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References
- 1) Preparation and Diels−Alder Reactivity of 1-Amino-3-siloxy-1,3-butadienes
- 2) On the Reactivity of 1-Amino-3-siloxy-1,3-dienes: Kinetics Investigation and Theoretical Interpretation
- 3) A Nine-Step Total Synthesis of (−)-Platencin
