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US 9,718,052 B2Granted
Catalysts and related processes for producing optically pure beta-lactones from aldehydes and compositions produced thereby
AssigneeThe University of Toledo
InventorYun-Ming Lin
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Abstract
Bi-functional cobalt-containing catalysts useful for making stereospecific compounds and compositions, along with methods of making, and uses thereof in the syntheses of optically pure β-lactones from aldehydes and ketene are described. Precursors, intermediates, compositions, and particular features of the use if the compositions, such as high enantiomeric selectivity, high yield and low mole percent of catalyst useful are provided.
Claims3
A method for making a β-lactone (12), represented by Scheme 4:
- the method comprising:
- combining ketene 1 and an aldehyde 11 in the presence of a catalyst 10 (5 mol %), and promoting a reaction −78° C. by bubbling the ketene 1 into a methylene chloride solution to produce β-lactone (12),
- wherein:
- the catalyst 10 has the structure
- the aldehyde (11);
- wherein R in structure (11) is selected from:
- 3-FC6H4, 3-ClC6H4, 2-ClC6H4, 2-FC6H4, PhCH2, PhCH2CH2, n-C6H13, and n-C11C23;
- the β-lactone (12) has an enantiomeric excess (ee) greater than or equal to 70%;
- and
- R represents, independently for each occurrence:
- alkyl, or aryl.
8 more elements
Dependencies are inferred from the claim text.