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Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

✍ Scribed by Ruijter, Eelco; Schültingkemper, Heike; Wessjohann, Ludger A.


Book ID
127089547
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
126 KB
Volume
70
Category
Article
ISSN
0022-3263

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Hetero Diels-Alder reactions of optically active 3-(p-tolylsulfinyl)-2furaldehyde with 1-methoxy-3-(trimethylsilyloxy)-buta-l,3-diene (Danishefsky's diene) in the presence of a Lewis acid has been examined. The reaction in the presence of 1.0 equiv, of Ln(OTf)3 (Ln = Yb, Nd and Sin) followed by acid