Rhodium-catalyzed formylation of organomercurials: Application to efficient polyol synthesis

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3205-3208

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

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; ETHER DERIVATIVE; FORMIC ACID; FORMIC ACID DERIVATIVE; ORGANOMERCURY COMPOUND; RHODIUM; TOLYPOTHRIX PENTAETHER;

ARTICLE; CATALYSIS; CHEMISTRY; CYANOBACTERIUM; SYNTHESIS;

ALCOHOLS; ALKENES; CATALYSIS; CYANOBACTERIA; ETHERS; FORMIC ACIDS; ORGANOMERCURY COMPOUNDS; RHODIUM;

EID: 0034609699     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006393o     Document Type: Article

References (36)

1. (a) Oishi, T.; Nakata, T. Synthesis 1990, 635-645.
2. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2012-2040.
3. (c) Schneider, C. Angew. Chem., Int. Ed. 1998, 37, 1375-1378.
4. (d) Smith, A. B.; Pitram, S. M. Org. Lett. 1999, 1, 2001-2004.
5. (a) Leighton, J. L.; O'Neil, D. N. J. Am. Chem. Soc. 1997, 119, 11118-11119.
6. (b) Sarraf, S. T.; Leighton, J. L. Tetrahedron Lett. 1998, 39, 6423-6426.
7. (c) Leighton, J. L.; Chapman, E. J. Am. Chem. Soc. 1997, 119, 12416-12417.
8. (a) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 403-405.
9. (b) Dreher, S. D.; Hornberger, K. R.; Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3197-3200.
10. (a) Larock, R. C. Tetrahedron 1982, 38, 1713-1754.
11. (b) Baird, W. C., Jr.; Hartgerink, R. L.; Surridge, J. H. J. Org. Chem. 1985, 50, 4601-4605.
12. (c) Walkup, R. D.; Park, G. J. Am. Chem. Soc. 1990, 112, 1597-1603.
13. (d) Kocovsky, P.; Grech, J. M.; Mitchell, W. L. Tetrahedron Lett. 1996, 37, 1125-1128.
14. Insertion/transmetalation of rhodium into the C-Hg bond would lead to essentially the same rhodium alkyl intermediate that is produced during our previously reported hydroformylation of enol acetals. See refs 2a,b.
15. Jongsma, T.; Challa, G.; Van Leeuwen, P. W. N. M. J. Organomet. Chem. 1991, 421, 121-128.
16. Two equivalents of acetic acid are formed in the combined oxymercuration and carbonylation. Control experiments showed that the aldehyde product was not affected by the presence of acetic acid.
17. 2.
18. (a) Brodersen, K. and Hummel, H.-U. in Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1987; Vol. 5, pp 1047-1097.
19. (a) Canty, A. J.; Barron, P.; Healy, P. C. J. Organomet. Chem. 1979, 179, 447-458.
20. (b) Michel, E.; Perie, J.; Lattes, A. J. Organomet. Chem. 1981, 204, 1-12.
21. (c) Al-Showiman, S. S. Inorg. Chim. Acta 1988, 141, 263-274.
22. (c) Black, D. S. C.; Deacon, G. B.; Edwards, G. L.; Gatehouse, B. M. Aust. J. Chem. 1993, 46, 1323-1336.
23. n structure is also possible.
24. Related DABCO-metal complexes have been reported: (a) Quagliano, J. V.; Banerjee, A. K.; Goedken, V. L.; Vallarino, L. M. J. Am. Chem. Soc. 1970, 92, 482-488.
25. (b) Yokobayashi, H.; Nagase, K.; Sone, K. Bull. Chem. Soc. Jpn. 1978, 51, 2569-2573.
26. Paoletti, P.; Stern, J. H.; Vacca, A. J. Phys. Chem. 1965, 69, 3759-3762.
27. 3.
28. (a) Mynderse, J. S.; Moore, R. E. Photochemistry 1979, 18, 1181.
29. (b) Mon, Y.; Kohchi, Y.; Suzuki, M. J. Org. Chem. 1991, 56, 631-637.
30. For syntheses of Tolypothrix pentaether, see ref 14b and (a) Nakata, T.; Suenaga, T.; Oishi, T. Tetrahedron Lett. 1989, 30, 6525-6528.
31. (b) Nakata, T.; Suenaga, T.; Nakashima, K.; Oishi, T. Tetrahedron Lett. 1989, 30, 6529-6532.
32. (c) Priepke, H.; Weigand, S.; Brückner, R. Liebigs Ann. 1997, 1635-1644.
33. (d) Priepke, H.; Brückner, R. Liebigs Ann. 1997, 1645-1655.
34. (e) Weigand, S.; Brückner, R. Liebigs Ann. 1997, 1657-1666.
35. (f) Allerheiligen, S.; Brückner, R. Liebigs Ann. 1997, 1667-1676.
36. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439.