A new strategy in enantioselective intramolecular hetero Diels-Alder reaction: catalytic double asymmetric induction during the tandem transetherification-intramolecular hetero Diels-Alder reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with rac-6-methyl-5-hepten-2-ol |
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| Authors: | Hidetaka KogaEiji Wada |
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| Affiliation: | a Department of Molecular and Material Science, Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan
b Institute of Advanced Material Study, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan |
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| Abstract: | An efficient catalytic double asymmetric induction during the tandem transetherification-intramolecular hetero Diels-Alder reaction has been developed. The enantioselective tandem reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with rac-6-methyl-5-hepten-2-ol has been achieved to provide methyl (2R,4aS,8aR)-3,4,4a,8a-tetrahydro-2,5,5-trimethyl-2H,5H-pyrano[4,3-b]-pyran-7-carboxylate in good yield with effective kinetic resolution (up to 95% selectivity), high diastereoselectivity (up to 92% de), and high enantioselectivity (up to 97% ee) in the presence of (S,S)-tert-Bu-bis(oxazoline)-Cu(SbF6)2 and 5 Å molecular sieves. |
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| Keywords: | double asymmetric induction intramolecular hetero Diels-Alder reaction chiral Lewis acid enantioselective reactions tandem reaction 1-oxa-1,3-butadiene transetherification molecular sieves |
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