CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE

HOFFMANN R, Mattay J (1995)
Liebigs Annalen (8): 1455-1461.

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Abstract
Sunthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported. Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-methone adducts 2 and 3. Further derivatization and olefination afforded four chiral dienes 12-15. Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19. Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting form the originally formed olefination product.
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HOFFMANN R, Mattay J. CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE. Liebigs Annalen. 1995;(8):1455-1461.
HOFFMANN, R., & Mattay, J. (1995). CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE. Liebigs Annalen(8), 1455-1461.
HOFFMANN, R., and Mattay, J. (1995). CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE. Liebigs Annalen, 1455-1461.
HOFFMANN, R., & Mattay, J., 1995. CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE. Liebigs Annalen, (8), p 1455-1461.
R. HOFFMANN and J. Mattay, “CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE”, Liebigs Annalen, 1995, pp. 1455-1461.
HOFFMANN, R., Mattay, J.: CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE. Liebigs Annalen. 1455-1461 (1995).
HOFFMANN, R, and Mattay, Jochen. “CYCLOADDITIONS .53. NEW SPIROCYCLIC CHIRAL DIENES - SYNTHESIS AND DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH N-PHENYLMALEIMIDE”. Liebigs Annalen 8 (1995): 1455-1461.
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