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Synthesis of Tetrahydro- and Dihydropyridines by Hetero Diels-Alder Reactions of Enantiopure α,β-Unsaturated Sulfinimines

✍ Scribed by Lutz F. Tietze; Ansgar Schuffenhauer

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
414 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Intermolecular hetero Diels-Alder reactions of the treatment with acetyl chloride or dimethyl sulfate. According to this procedure, 21 gives either N-acetyltetrahydropyridine enantiopure sulfinimine 11 with the enol ethers 12-16 at 20 °C and 11 kbar lead to the tetrahydropyridines 18-22 in high 29 or the N-methyldihydropyridine 32. The intramolecular Diels-Alder reaction of 26 yields 27, which is transformed yield, with very good to good endo/exo selectivities, and with an induced diastereoselectivity of up to 2.1:1. The sulfinyl into 33 and 34, respectively. group in the adducts can be removed with MeLi followed by

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