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Ytterbium triflate-catalyzed asymmetric hetero Diels-Alder cycloaddition of a 1-thiabuta-1,3-diene with a chiral N-acryloyloxazolidinone dienophile. Diastereoface control by solvents or achiral additives

โœ Scribed by Takao Saito; Mikako Kawamura; Jun-ichi Nishimura


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

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โœฆ Synopsis


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 altering the auxiliary chirality for the asymmetric induction.


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Lewis acid-catalyzed asymmetric hetero D
โœ Takao Saito; Hirofumi Suda; Mikako Kawamura; Jun-ichi Nishimura; Akemi Yamaya ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 235 KB

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 dramatica