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Enhanced stereoselectivity in aqueous intramolecular hetero Diels-Alder cycloaddition of chiral acylnitroso compounds

✍ Scribed by Masaichi Naruse; Sakae Aoyagi; Chihiro Kibayashi


Book ID
104215614
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
310 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis


In an aqueous medium, intramolecular hetero Die&Alder cycloadditions of the chiral acylnitroso compounds, generated from the chiral hydroxamic acids by in situ periodate oxidation, shows a pronounced enhancement of the trans selectivity compared with the results obtained by employing nonaqueous conditions.


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Inter- and intramolecular hetero diels-a
✍ Tietze, Lutz F. ;Utecht, Jens πŸ“‚ Article πŸ“… 1992 πŸ› Wiley (John Wiley & Sons) 🌐 English βš– 542 KB

Azabutadienes f Isoxazoles f Tetrahydropyridines 1 Diels-Alder reactions / Sequential transformations Condensation of aldehydes 1 ae with 5-amino-3-methylisoxazole (4) gives the corresponding imines 5a-e with a 2-aza-1,3-butadiene moiety, which cyclize selctively, e.g. 5a to form the trans-fused tet