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2002 Diastereoselective syntheses Diastereoselective syntheses O 0031 Synthesis and Dienophilic Behavior of Enantiomerically Pure (E)-2-p-Tolylsulfi- nylacrylonitrile Derivatives. — Enantiomerically pure acetal (III) is prepared by Knoevenagel condensation of (R)-sulfoxide (I) with aldehyde (II) and is hydrolyzed to give the corresponding aldehyde (IV). The cycloaddition reaction of acetal (III) with cyclopentadiene is studied in detail by varying the type and amount of Lewis acid, the temperature and the reaction time. It is found that best results are obtained in the pres- ence of Eu(fod) 3 leading to high π-facial selectivity. After extended reaction times, the π-facial selectivity becomes almost complete. The endo/exo selectivity (max. 80:20) is only moderate. The reactivity of aldehyde (IV) is higher but it reacts with less stereo- selectivity than acetal (III) and with almost no endo/exo selectivity. — (GARCIA RUANO*, J. L.; GONZALEZ GUTIERREZ, L.; MARTIN CASTRO, A. M.; YUSTE, F.; Tetrahedron: Asymmetry 13 (2002) 18, 2003-2010; Dep. Quim. Org., Fac. Cienc., Univ. Auton., Cantoblanco, E-28049 Madrid, Spain; Eng.) — Klein 07- 035

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Page 1: Synthesis and Dienophilic Behavior of Enantiomerically Pure (E)-2-p-Tolylsulfinylacrylonitrile Derivatives

2002 Diastereoselective syntheses

Diastereoselective synthesesO 0031 Synthesis and Dienophilic Behavior of Enantiomerically Pure (E)-2-p-Tolylsulfi-

nylacrylonitrile Derivatives. — Enantiomerically pure acetal (III) is prepared by Knoevenagel condensation of (R)-sulfoxide (I) with aldehyde (II) and is hydrolyzed to give the corresponding aldehyde (IV). The cycloaddition reaction of acetal (III) with cyclopentadiene is studied in detail by varying the type and amount of Lewis acid, the temperature and the reaction time. It is found that best results are obtained in the pres-ence of Eu(fod)3 leading to high π-facial selectivity. After extended reaction times, the π-facial selectivity becomes almost complete. The endo/exo selectivity (max. 80:20) is only moderate. The reactivity of aldehyde (IV) is higher but it reacts with less stereo-selectivity than acetal (III) and with almost no endo/exo selectivity. — (GARCIA RUANO*, J. L.; GONZALEZ GUTIERREZ, L.; MARTIN CASTRO, A. M.; YUSTE, F.; Tetrahedron: Asymmetry 13 (2002) 18, 2003-2010; Dep. Quim. Org., Fac. Cienc., Univ. Auton., Cantoblanco, E-28049 Madrid, Spain; Eng.) — Klein

07- 035

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