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2-Phenylsulfonyl 1,3-dienes in asymmetric diels-alder reactions with chiral enamines and enol ethers

✍ Scribed by Jan-E. Bäckvall; Frode Rise

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
137 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Z-Phenylsulfonyl 1,3-dienes underwent diastereoselective inverse electron demand Diels-Alder reactions with enamines (up to 73% de) and enol ethers (up to 50% de). 2-Phenylsulfonyl 1,3-dienes are useful building blocks in organic synthesis,'" and several methods for their preparation have recently been reported. 1*2,4-6 One important property of these dienes is that they show a dual eIectron demand in Diels-Alder reactions and thus undergo cycloaddition with both electron deficient and electron rich olefins. Electron rich olefins such as enol ethers, enamines and also indole magnesium salts give highly regioselective cycloadditions with these dienes. 2+3 With the aim of obtaining diastereoselective cycloadditions we have now studied the reaction of 2-phenylsulfonyl 1,3-clienes with chiral enamines and enol ethers.

We previously reported that enol ethers undergo [4+2] cycloaddition with 2-phenylsulfonyl-1,3-butadiene.

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