Phase transfer catalysts

• US 8,692,000 B2
• Filed: 10/27/2011
• Issued: 04/08/2014
• Est. Priority Date: 10/28/2010
• Status: Expired due to Fees

• Current Assignee: National University of Singapore
• Original Assignee: National University of Singapore
• Inventors: Fu, Xiao, Tan, Choon Hong, Huang, Kuo Wei, Ma, Ting
• Primary Examiner(s): SHTERENGARTS, SAMANTHA L
• Application Number:
  US13/881,819
• Publication Number:
  US 20130217889A1
• Time in Patent Office: 894 Days
• Field of Search: 560/35, 548/312.7
• US Class Current: 548/312.7
• CPC Class Codes: B01J 31/0244 with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
• CPC Class Codes: B01J 31/0271 also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
• CPC Class Codes: B01J 31/0275 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
• CPC Class Codes: C07C 251/24 having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 233/44 Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 235/30 Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 307/46 Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
• CPC Class Codes: C07D 307/54 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 333/24 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Compounds of formula (I): wherein R₁ to R₈, and X⁻ are defined herein. Also disclosed are methods of making and using these compounds.

Claims

1. A compound of formula (I):

2. The compound of claim 1, wherein R₁ is identical to R₈, R₂ is identical to R₇, R₃ is identical to R₆, and R₄ is identical to R₅.

3. The compound of claim 2, wherein all the carbon atoms to which R₂, R₃, R₆, and R₇ are attached have an R or S configuration.

4. The compound of claim 3, wherein all the carbon atoms to which R₂, R₃, R₆, and R₇ are attached have an R configuration, or all of them have a S configuration.

5. The compound of claim 4, wherein each of R₂, R₃, R₆, and R₇, independently, is aryl or heteroaryl.

6. The compound of claim 4, wherein R₂ and R₃, together with the two carbon atoms to which they are attached, form C₄-C₂₀ cycloalkyl;

and R₆ and R₇, together with the two carbon atoms to which they are attached, form C₄-C₂₀ cycloalkyl.

7. The compound of claim 4, wherein each of R₁, R₄, R₅, and R₈, independently, is C₁-C₁₀ alkyl.

8. The compound of claim 1, wherein the compound is one of Compounds 1a, 1b, 1c, 1d, 1e, and 1f as shown below:

9. The compound of claim 1, wherein R₁ is identical to R₈, each of R₂ and R₇ is H, and R₄ is identical to R₅.

10. The compound of claim 9, wherein all the carbon atoms to which R₃ and R₆ are attached have an R or S configuration.

11. The compound of claim 10, wherein each of R₃ and R₆, independently, is aryl or heteroaryl.

12. The compound of claim 10, wherein each of R₁, R₄, R₅, and R₈, independently, is C₁-C₁₀ alkyl.

13. The compound of claim 1, wherein R₁ is identical to R₈, each of R₃ and R₆ is H, and R₄ is identical to R₅.

14. The compound of claim 13, wherein all the carbon atoms to which R₂ and R₇ are attached have an R or S configuration.

15. The compound of claim 14, wherein each of R₂ and R₇, independently, is aryl or heteroaryl.

16. The compound of claim 14, wherein each of R₁, R₄, R₅, and R₈, independently, is C₁-C₁₀ alkyl.

19. A method of preparing a chiral compound of formula (IV):

20. The method of claim 19, wherein the catalyst is one of Compounds 1a, 1b, 1c, 1d, 1e, and 1f as shown below:

17. A method of preparing a compound of formula (I):

18. The method of claim 17, wherein the compound of formula (I) is one of Compounds 1a, 1b, 1c, 1d, 1e, and 1f as shown below: