Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN3. An efficient, catalytic route to 1,2-amino alcohols

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7420-7421

  Larrow, Jay F ^a   Schaus, Scott E ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; DRUG PURIFICATION; ENANTIOMER; TECHNIQUE;

EID: 0029757771     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961708+     Document Type: Article

References (35)

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15. Chang, H.-T.; Sharpless, K. B. Tetrahedron Lett. 1996, 37, 3219. A breakthrough in the direct, asymmetric catalytic synthesis of amino alcohols from alkenes was also reported recently by the Sharpless group: Li, G.; Chang, H.-T.: Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
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29. 3 (330 μL, 2.5 mmol). The reaction was allowed to stir at 0-2 °C for 18 h, upon which time the remaining epoxide was removed by rotary evaporation, and the desired product was vacuum distilled (24 °C/ <1 mm Hg) into a cooled collection flask to yield 0.425 g (2.45 mmol, 98%) of a colorless oil. Chiral GC analysis (Cyclodex-B) indicated that the 1-azido-2-trimethylsiloxypropane was obtained in 97% ee.
30. rel actually represent lower limits. For leading references on kinetic resolution, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. M. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; pp 395-415. (b) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Interscience: New York, 1987; Vol. 14, p 249.
31. rel actually represent lower limits. For leading references on kinetic resolution, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. M. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; pp 395-415. (b) Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Interscience: New York, 1987; Vol. 14, p 249.
32. (R)-PMPA has recently been synthesized from the chiral pool utilizing D-(-)-lactic acid as the enantiopure starting material: Holy, A.; Masqjídková, M. Collect. Czech. Chem. Commun. 1995, 60, 1196.
33. For preparation of 9-[2-(hydroxypropyl)]adenine see: Schaeffer, H. J.; Vince, R. J. Med. Chem. 1967, 10, 689.
34. For similar phosphonomethoxytosylate alkylation reactions, see: Yu, K-L; Bronson, J. J.; Yang, H.; Patick, A.; Alam, M.; Brankovan, V.; Datema, R.; Hitchcock, M. J. M.; Martin, J. C. J. Med. Chem. 1992, 35, 2958.
35. 4 but were identical to previous catalyst batches in all other respects. For ligand preparation, see: Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939. Both enantiomers of the ligand are also commercially available (Aldrich).