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Lewis acid-catalyzed asymmetric hetero Diels-Alder cycloaddition of a 1-Thiabuta-1,3-diene with Chiral N-Acryloyl- and N-Crotonoyl-oxazolidinone dienophiles

✍ Scribed by Takao Saito; Hirofumi Suda; Mikako Kawamura; Jun-ichi Nishimura; Akemi Yamaya

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
235 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Me2AICI -and TiCl4-catalyzed asymmetric hetero Diels-Alder cycloaddition reactions of 2,4-diphenyl-l-thiabuta-l,3-diene with (S)-N-acryloyl-and (S)-N-crotonoyl-4-benzyl-l,3-oxazolidin-2one dienophiles are described in which not only the sense of the n-facial selectivity but also the degree dramatically varied as a function of stoichiometry of the added Lewis acids.

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Ytterbium triflate-catalyzed asymmetric
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✍ Takao Saito; Mikako Kawamura; Jun-ichi Nishimura πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 182 KB

Ytterbium triflate [Yb(OTf)3]-catalyzed asymmetric hetero Diels-Alder cycloaddition reaction of 2,4-diphenyl-l-thiabuta-l,3-diene with (S)-N-acryloyl-4-benzyl-l,3-oxazolidin-2-one is described in which the sense of the ~-faciai selectivity can be controlled by solvents or additives employed without

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A crude, crystalline mixture 20a/20b (m.p. 102-103") was treated in analogous manner as that obtained from the reaction of cyclopentadiene with dienophile 2. 1,4-Di-O-tosyl-2,3-0-isopropylidene-~-threitol in y-pipecoline was refluxed for 3 h, and then the resulting product was hydrolyred to afford 1