Oxymercuration of homoallylic alcohol derived hemiacetals: Diastereoselective synthesis of protected 1,3-diols

Organic Letters

Volumn 2, Issue 3, 2000, Pages 403-405

  Sarraf, Stella T ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ORGANOMERCURY COMPOUND;

ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

ACETALS; ALCOHOLS; ORGANOMERCURY COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS;

EID: 0034628215     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991370z     Document Type: Article

References (15)

1. (a) Leighton, J. L.; O'Neil, D. N. J. Am. Chem. Soc. 1997, 119, 11118-11119.
2. (b) Leighton, J. L.; Chapman, E. J. Am. Chem. Soc. 1997, 119, 12416-12417.
3. (c) Sarraf, S. T.; Leighton, J. L. Tetrahedron Lett. 1998, 39, 6423-6426.
4. Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
5. We have employed the method of Petasis: Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141-144. While effective, the method is less amenable to larger scales.
6. For reviews of oxymercuration reactions, see: (a) Larock, R. C. Solvomercuration/Demercuration Reactions in Organic Synthesis; Springer: New York, 1986.
7. (b) Larock, R. C. In Comprehensive Organometallic Chemistry II; McKillop, A., Vol. Ed., and Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 11, pp 389-435.
8. Overman, L. E.; Campbell, C. R. J. Org. Chem. 1974, 39, 1474-1481.
9. A related example involving ketone hemiacetals has been recorded. See: Kitching, W.; Lewis, J. A.; Fletcher, M. T.; de Voss, J. J.; Drew, R. A. I.; Moore, C. J. J. Chem. Soc., Chem. Commun. 1986, 855-856.
10. (a) Bloodworth, A. J.; Shah, A. J. Chem. Soc., Chem. Commun. 1991, 947-948.
11. (b) Bloodworth, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428-429.
12. All new compounds were characterized spectroscopically. Stereochemical determinations were derived from NOE experiments. See the Supporting Information for details.
13. Bowmaker, G. A.; Churakov, A. V.; Harris, R. K.; Oh, S.-W. J. Organomet. Chem. 1998, 550, 89-99.
14. We have developed an alternative procedure for the preparation of HgClOAc. See the Supporting Information for details.
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