Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7937-7940

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

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; EPEREZOLID; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; TECHNIQUE;

EID: 0030605102     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01835-7     Document Type: Article

References (12)

1. (1) For a timely review, see: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn., 1995, 68, 36.
2. (2) (a) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
3. (b) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
4. 3 (330 μL, 2.5 mmol) was added over the next 16 h at rt, and the reaction was allowed to stir an additional 24 h. Product was isolated by vacuum distillation (50 °C / 0.5 mm Hg) into a cooled collection flask to yield 1.04 g (76% by GC analysis) of 2 as a colorless oil. Chiral GC analysis of the corresponding azido alcohol (γ-TA, 80 °C for 19 min, 1 °C / min to 95 °C) indicated that 2 was produced in 97% ee.
5. (4) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc., in press.
6. (5) CAUTION: Although problems have never been encountered in our labs in experiments carried out at multigram scale, low molecular weight organic azide compounds should be handled with extreme caution due to their possible shock sensitivity.
7. (6) The (salen)CrCl complex 7 has been shown to transfer chloride to epoxides with low enantioselectivity. See ref 3.
8. (7) (a) Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673.
9. (b) Barbachyn, M. R.; Hutchinson, D. K.; Brickner, S. J.; Cynamon, M. H.; Kilburn, J. O.; Klemens, S. P.; Glickman, S. E.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 680.
10. 3, 100 MHz) δ 170.44, 170.40, 72.0, 43.4, 40.6, 23.1, 20.9.
11. +: 116.0711; found: 116.0714.
12. 7a as an off white solid.