Diels-alder reaction of aldehydes with simple dienes

Details Diels-alder reaction of aldehydes with simple dienes Diels-alder reaction of aldehydes with simple dienes

1998-01-19

2000-09-05

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30900

Patent

active

061145483

ABSTRACT:
The invention concerns Diels-Alder reactions between non-activated aldehydes RCHO in which R is a C1-C10 aliphatic group or phenyl group, which is unsubstituted or substituted with one or more C1-C5 alkyl groups or one other functional group, with simple aliphatic dienes R.sub.1 CH.dbd.CR.sub.2 --CR.sub.3 .dbd.CHR.sub.4 in which R.sub.1 -R.sub.4 are H or C1-C5 alkyl groups using as a catalyst a perfluorinated organic sulphonic acid or a Bronsted acid derivative thereof. The reaction leads to dihydropyrans of the structure below in which R1-R4 have the meaning indicated above.
The preferred perfluorinated organic sulfonic acids are perfluorooctanesulphonic acid, triflic acid, Nafion or a Bronsted acid derivative of triflic acid. ##STR1## The preferred aldehydes are those wherein R is a C2-C6 aliphatic group or a phenyl group which is unsubstituted or mono-substituted with C1-C3 alkyl or with 4-Cl, 4-nitro or 3-methoxy. The preferred dienes are those wherein the groups R.sub.1 -R.sub.4 are H or methyl.

REFERENCES:
patent: 4709085 (1987-11-01), Nugent et al.
patent: 4847392 (1989-07-01), Gassman et al.
Chemical Abstracts, vol. 1, No. 7, Aug. 13, 1979, Columbus, Ohio, US; Abstract No. 56685y, XP002063880.
Chemical Abstracts, vol. 126, No. 26, Jun. 30, 1997, Columbus, Ohio, US; Abstract No. 343460t, XP002063881.
Chemical Abstracts, vol. 127, No. 9, Sep. 1, 1997, Columbus, Ohio, US; Abstract No. 121610y, XP002063882.
J. Inanaga et al.; New J. Chem., vol. 19, 1995, pp. 707-712, XP002049944.
S. Oi et al., Tetrahedron Letters, vol. 37, No. 35, 1996, Oxford GB, pp. 6351-6354, XP002063879.
H. Griengl et al. Monatshofte for Chemie, vol. 107, 1976; Wein At, pp. 675-684, XP002063877.
M.F. Ansell et al.; Journal of the Chemical Society, Chemical Communications, 1972, Letchworth GB, pp. 73990740. XP002063877.
Catalyzed Adhesions of Nucleophilic Alkenes to C = pp. 534-561.
Tetrahedron Letters, vol. 34, No. 15; pp. 2409-2413.
Synlett, Mar. 1996; A New Scandium Complex as an Extremely Active Acylation Catalyst; pp. 265-266.
Tetrahedron Letters, vol. 37, No. 35; pp. 6351-6354, 1996.
Catalyzed Additions of Nucleophilic Alkenes to C=X; 2.1 The Prins and Carbonyl Ene Reactions; Barry B. Snider, p. 527-533.
Synthesis, Jun. 1994, Asymmetric Hetero Diels-Alder Reactions, p. 535-551.
New J. Chem. 1995, 19, p. 707-712; Achiral and Chiral Lanthanide Salts of Superacids as Novel Lewis Acid Catalysts in Organic Synthesis.
Synlett, Sep. 1994, p. 689-701.
T. Imamols/Academic Press, p. 102-111.
New J. Chem. 1995, 19, 713-722 p. 973-977.

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