Asymmetric hydroformylation process

Details Asymmetric hydroformylation process Asymmetric hydroformylation process

1973-02-16

1981-05-19

Milestone, Norma S.

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

Organic compounds

Carboxylic acid esters

560250, 560254, 560255, 560266, 564219, 564342, 568429, 568451, 568452, 546237, 546340, C07C 4550

Patent

active

042686881

ABSTRACT:
This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.
This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.
The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g., phosphine, arsine, stibine, or amine. The coordination compound may contain one or more additional ligands, which may be neutral or which may possess negative charges such as carbon monoxide, hydrogen, olefins and diolefins, and halides.

REFERENCES:
patent: 3527809 (1970-09-01), Pruett et al.
patent: 3641076 (1972-02-01), Booth
C. Botteghi et al., Chimia, 26, No. 3, Mar. 1972, pp. 141-143.
JACS 94: 6429-6433, (1972), Kagan et al.

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