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Communication | Regular issue | Vol 31, No. 7, 1990, pp.1229-1232
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5436
Use of 1,3-Dioxin-4-ones and Their Related Compounds in Synthesis. 27. Novel Asymmetric Hetero-Diels-Alder Reaction Using Chiral Spiro 5-Methylene-1,3-dioxane-4,6-diones Having 1-Methone at the 2-Position

Masayuki Sato,* Kazuya Kano, Noritaka Kitazawa, Hiroyuki Hisamichi, and Chikara Kaneko*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Diastereofacially selective heter-Diels-Alder reaction of spiro (E or Z)-5-arylidene-1,3-dioxane-4,6-diones and 2-methoxypropene was studied. The dihydropyrans thus obtained were converted to optically active β-arylated δ-oxohexanoic acids. The diastereofacil selectivity fo the hetero-Diels-Alder reactions is explained by the sofa-conformation of the heterodienes which accepts the dienophile at the convex α-side preferentially.