Compounds containing oxazolidinone moiety and uses thereof

1. A compound of the formula:

wherein

each of R 3 and R 4 is independently hydrogen or —OR c , where R c is a non-ring forming hydroxy protecting group, or R 3 and R 4 together with the carbon atoms to which they are attached form an optionally substituted heterocyclyl;

each of R 5 and R 6 is independently hydrogen or alkyl; and one of X 1 and X 2 is O and the other is NR 7 , where

R 7 is hydrogen, alkyl, aryl, —(R 8 ) n —C(═O)—R 9 , or nitrogen protecting group,

where

n is 0 or 1;

R 8 is alkylene, and

R 9 is hydroxy, alkyl, alkoxy, aryl, aryloxy, or —NR 3 R b , where each of R 2 and R b is independently hydrogen or alkyl.

2. The compound according to claim 1 , wherein the relative stereochemiswy of R 3 and R 4 is a cis-configuration.

3. The compound according to claim 1 of the formula:

or a sterecisomer thereof,

wherein

R 3 R 4 , and R 7 are those defined in claim 1 .

4. The compound according to claim 3 , wherein R 3 and R 4 together wit the carbon atoms to which they are attached form an optionally substituted heterocyclyl.

5. The compound according to claim 4 of the formula:

or a sterecisomer thereof,

wherein

R 7 is that defined in claim 1 ; and

each of R 10 and R 11 is independently selected from the group consisting of hydrogen, alkyl, aralkyl and aryl.

6. The compound according to claim 2 , wherein R 3 and R 4 together with the carbon atoms to which they are attached form an optionally substituted nitrogen atom containing heterocyclyl.

7. The compound according to claim 6 of the formula:

wherein

R 1, R 2 , R 5 , R 6 , X 1 , and X 2 , are those defined in claim 1 ; and one of X 3 and X 4 is O and the other is NR 7 , where R 7 is defined in claim 1 .

8. A method for producing a spiro-bicyclic compound of the formula:

wherein

each of R 3 and R 4 is independently hydrogen or —OR c , where R c is a non-ring forming hydroxy protecting group, or R 3 and R 4 together with the carbon atoms to which they are attached to form an optionally substituted heterocyclyl; and

R 7 is selected from the group consisting of hydrogen, alkyl, and, —(R 8 ) n —C(═O)—R 9 , and another nitrogen protecting group,

where

n is 0 or 1,

R 8 is alkylene, and

R 9 is hydroxy, alkyl, alkoxy, and, aryloxy and —NR a R b , where R a and R b is independently hydrogen or alkyl;

said method comprising:

(a) contacting a carbohydrate selected from glucose and fructose with an amine under condition sufficient to produce an amino tetrahydroxy carbohydrate;

(b) protecting two hydroxy groups by contacting the amino tetrahydroxy carbohydrate wit a hydroxy protecting group under conditions sufficient to produce a dihydroxy-protected amino dihydroxy carbohydrate;

(c) forming a heterocyclic moiety by contacting the dihydroxy-protected amino dihydroxy carbohydrate with an activated carbonate under conditions sufficient to produce a hydroxy spiro-bicyclic compound; and

(d) oxidizing the hydroxy group by contacting the hydroxy spiro-bicyclic compound with an oxidizing agent under conditions sufficient to produce the spiro-bicyche compound of Formula IA.

9. The method of claim 8 , wherein the spiro-bicyclic compound is enantiomerically enriched chiral compound.

10. The method of claim 9 , wherein the carbohydrate is glucose.

11. The method of claim 10 , wherein the carbohydrate is D-glucose.

12. The method of claim 10 , wherein the enantiomerically enriched spiro-bicyclic compound is of the formula:

or stereoisomers thereof,

where R 3 , R 4 and R 7 are those defined in claim 8 .

13. The method of claim 12 , wherein the enantiomerically enriched spiro-bicyclic compound is of the formula:

or a stereoisomers thereof,

wherein

R 7 is that defined in claim 8 ; and each of R 10 and R 11 is independently selected from the group consisting of hydrogen, alkyl, aralkyl and aryl.

14. The method of claim 8 , wherein the activated carbonate is selected from the group consisting of phosgene, triphosgene and a haloformate.

15. The method of claim 8 , wherein the amine is diaralkyl amine.

16. The method of claim 15 further comprising removing aralkyl groups from the amino nitrogen by contacting the dihydroxy-protected amino dihydroxy carbohydrate with hydrogen in the presence of a hydrogenation catalyst under conditions sufficient to produce a dihydroxy-protected free-amino carbohydrate prior to said heterocyclic moiety forming step (c).

17. A method for producing an epoxide from an olefin comprising admixing a ketone compound of claim 1 , an olefin, and an oxidizing agent under conditions sufficient to produce the epoxide.

18. The method of claim 17 , wherein the olefin comprises a chiral or a pro-chiral center.

19. The method of claim 18 , wherein the ketone compound of claim 1 is an enantiomerically enriched chiral ketone compound.

20. The method of claim 19 , wherein the epoxide is enariomerically enriched.

21. The method of claim 20 , wherein the olefin is a cis-olefin or a terminal olefin.

22. The method of claim 19 , wherein the enantiomerically enriched chiral ketone is of the formula:

or a sterecisomer thereof,

wherein

R 7 is that defined in claim 1 ; and

each of R 10 and R 11 is independently selected from the group consisting of hydrogen, alkyl, aralkyl and aryl.

23. The method of claim 17 , wherein said oxidizing agent is selected from the group consisting of peracids, hydrogen peroxide, sodium hypochlorite, potassium peroxormonosulfate, sodium perborate and hypofluoride (HOF).

24. The method of claim 23 , wherein said oxidizing agent is potassium peroxomonosulfate.

25. The method of claim 17 , wherein said admixture further comprises a base.

26. The method of claim 17 further comprising maintaining pH of the admixture within the range of from about pH 5 to about pH 14,

27. The method of claim 17 , wherein said asymmetric epoxide is produced in an enantiomeric excess of at least about 80% ee.

28. A method for stereoselecrively epoxidizing a cis-olefin or a terminal olefin comprising the steps of admixing a chiral ketone compound of claim 1 , the cis- or the terminal olefin, and an oxidizing agent under conditions sufficient to produce an asymmetric epoxide in at least about 80% ee.

29. The method of claim 28 , wherein said chiral ketone is of the formula:

and a sterecisomer thereof,

wherein

R 7 is that defined in claim 1 each of R 10 and R 11 is independently selected from the group consisting of hydrogen, alkyl, aralkyl and aryl.