Catalysts and related processes for producing optically pure beta-lactones from aldehydes and compositions produced thereby

Patent metadata

Field	Value
Publication number	US-9718052-B2
Application number	US-201615099995-A
Country	US
Kind code	B2
Filing date	Apr 15, 2016
Priority date	Sep 4, 2009
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

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.

First claim

What is claimed is:

1. 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-FC 6 H 4 , 3-ClC 6 H 4 , 2-ClC 6 H 4 , 2-FC 6 H 4 , PhCH 2 , PhCH 2 CH 2 , n-C 6 H 13 , and n-C 11 C 23 ;
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.

2. The method of claim 1 , wherein the β-lactone (12) has an enantiomeric excess (ee) greater than or equal to 70%.

3. The method of claim 1 , wherein the β-lactone (12) has an enantiomeric excess (ee) greater than or equal to 99%.

Assignees

• Univ Toledo

Inventors

• Lin yun-ming

Classifications

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• B01J31/2295 Primary

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• B01J2531/845

  Cobalt · CPC title

• C07D453/04 Primary

  having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine · CPC title

• C07F15/065

  without a metal-carbon linkage · CPC title