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Asymmetric synthesis and applications of chiral 3-phenylsulfinyl-3-sulfolenes

✍ Scribed by Shang-Shing P. Chou; Pi-Wei Liang

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
175 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The chiral 3-phenylsulfinyl-3-sulfolene 2 (S-form) was efficiently prepared in 92% ee by oxidation of sulfide 1 with Ti(O-i-Pr) 4 /(-)-DET/t-BuOOH (1:4:1) in toluene. Thermal desulfonylation of 2 gave chiral diene 3. Deprotonation of 2 by BuLi followed by the reaction with alkyl halides gave regiospecifically the C-2 alkylated 3-sulfolenes 4-8. Intramolecular Diels-Alder reactions of compounds 7 and 8 gave the bicyclic products 9-11. Thermal desulfonylation of 4 generated chiral dienyl sulfoxide 15, which underwent thermal and Lewis acid-catalyzed Diels-Alder reactions with good regio-, stereo-and enantioselectivity.

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Facile Synthesis of 3-Aroyl-3-sulfolenes Through Cycloadditions of Arylnitrile Oxides and 3-Sulfolene. -Aromatic oximes (II) are converted to the corresponding arylnitrile oxides which undergo 1,3-dipolar cycladdition reactions with 3-sulfolene (I) to yield fused ring heterocycles (III)