Practical access to highly enantioenriched c-3 building blocks via hydrolytic kinetic resolution

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6776-6777

  Furrow, Michael E ^a   Schaus, Scott E ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000180260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981332d     Document Type: Article

References (15)

1. Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1987; Vol, 14, pp 249-330.
2. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
3. (S, S)-N, N′-Bis(3, 5-di-tert-butylsalicylidene)-l, 2-cyclohexaneaiaminocobalt(II): Aldrich catalog no. 47, 460-6. (R, R)-N, N-Bis(3, 5-di-tert-butyl-salicylidene)-l, 2-cyclohexanediaminocobalt(II): Aldrich catalog no. 47, 459-2. The corresponding Co(III) complex 1 is generated either in situ in the HKR or in a discrete step by exposure of the Co(II) complex to air in the presence of AcOH. See the Supporting Information for complete experimental details.
4. For an alternative route to enantioenriched epichlorohydrin employing asymmetric catalysis, see: Takeichi, T.; Arihara, M.; Ishimori, M.; Tsuruta, T. Tetrahedron 1980, 36, 3391.
5. For the synthesis of enantiopure epichlorohydrin by enzymatic resolution of 2, 3-dichloro-1-propanol, see: Kasai, N.; Tsujimura, K.; Suzuki, T. Jpn. Patent JP 02 257 895, 1990;
6. Chem. Abstr. 1991, 114, 41064q.
7. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937.
8. For the synthesis of 3 and 4 by asymmetric dihydroxylation, see: Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448.
9. For a review, see: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
10. For a review of the synthetic applications of glycidol and glycidol derivatives, see: Hansen, R. H. Chem. Rev. 1991, 91, 437.
11. For the synthesis of glycidol by asymmetric epoxidation of allyl alcohol, see: (a) Klunder, J. M.; Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 3710.
12. (b) Hanson, R. M.; Ko, S. Y.; Gao, Y.; Masamune, H.; Klunder, J. M.; Sharpless, K B. J. Am. Chem. Soc. 1987, 109, 5765.
13. For the enzymatic resolution of benzyl glyeidyl ether, see: (a) Weijers, C. A. G. M. Tetrahedron: Asymmetry 1997, 8, 639.
14. (b) Pederson, R. L.; Liu, K. K.-C.; Rutan, J. F.; Chen, L.; Wong, C.-H. J. Org. Chem. 1990, 55, 4897.
15. For the enzymatic resolution of glyeidyl butyrate, see: Ladner, W. E.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 7250.