Process for producing 2-substituted optically active 2,3-dihydro

Details Process for producing 2-substituted optically active 2,3-dihydro Process for producing 2-substituted optically active 2,3-dihydro

1996-07-08

1998-06-16

Nazario-Gonzalez, Porfirio

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

502150, 549427, 556 54, C07D31500, C07F 700, B01J 3100

Patent

active

057672954

ABSTRACT:
The invention provides an efficient process for producing a 2-substituted optically active 2,3-dihydro-4H-pyran-4-one comprising subjecting an aldehyde, which is not bulky and cannot be expected an electronic interaction with a catalyst, such as acetaldehyde, and a Danishefsky diene to a highly enantio-selective asymmetric hetero Diels-Alder reaction in the presence of an asymmetric catalyst readily obtainable from inexpensive starting materials.

REFERENCES:
Keck et al., Journal of Organic Chemistry, vol. 60, No. 19, pp. 5998-5999, Sep. 22, 1995.
Chemical Abstracts 124:55733 (1996).
Chemical Abstracts 122:9813 (1995).
Chemical Abstracts 108:37584 (1988).
Chemical Abstracts 99:5480 (1983).
Corey et al., Enantioselective Mukaiyama-Aldol and Aldol-Dihydropyrone Annulation Reactions Catalyzed by a Tryptophan Derived Oxazaborolidine, Tetrahedron Letters, vol. 33, 1992, pp. 6907-6910.
Keck et al., Pronounced Solvent and Concentration Effects in an Enantioselective Mukaiyama Aldol Condensation Using BINOL-Titanium(IV) Catalysts, J. Am. Chem. Soc., vol. 117, 1995, pp. 2363-2364.
Matsukawa et al., Highly Enantioselective Catalysis of the Mukaiyama Aldol Reaction by BINOL-Ti Perfluorophenoxide and Enoxysilacyclobutane, Tetrahedron; Asymmetry, vol. 6, No. 10, 1995, pp. 2571-2574.

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