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 (cas 1335-09-7)

Add time:08/30/2019    Source:sciencedirect.com

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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