Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2- isoborneolsulfonylaminocyclohexane-catalyzed addition of organozincs to ketones

Tetrahedron Asymmetry

Volumn 16, Issue 20, 2005, Pages 3341-3344

  Forrat, Vicente J ^a   Ramón, Diego J ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ARENESULFONYLAMINO 2 ISOBORNEOLSULFONYLAMINOCYCLOHEXANE; ALCOHOL DERIVATIVE; ALKENYL GROUP; ALKYL GROUP; ALLYL COMPOUND; CYCLOHEXYLAMINE DERIVATIVE; KETONE DERIVATIVE; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; HYDROGEN BOND; PRIORITY JOURNAL; SYNTHESIS;

EID: 27744469991     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.08.031     Document Type: Article

References (40)

1. G. Helmchen R.W. Hoffmann J. Mulzer E. Schaumann Stereoselective synthesis (Houben-Weyl) Vols. 1-10 1996 Thieme Stuttgart
2. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vols. 1-3 1999 Springer Berlin
3. K. Fuji Chem. Rev. 93 1993 2037 2066
4. E.J. Corey, and A. Guzmán-Pérez Angew. Chem., Int. Ed. 37 1998 388 401
5. D.J. Ramón, and M. Yus Curr. Org. Chem. 8 2004 149 183
6. J. Christoffers A. Baro Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis 2005 Wiley-VCH Weinheim
7. M. Yus, and D.J. Ramón Recent Res. Dev. Org. Chem. 6 2002 297 378
8. D.J. Ramón, and M. Yus J. Christoffers A. Baro Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis 2005 Wiley-VCH Weinheim 207 241
9. D.J. Ramón, and M. Yus Tetrahedron: Asymmetry 8 1997 2479 2496
10. For a review, see: Yus, M.; Ramón. D. J. Pure Appl. Chem., in press.
11. D.J. Ramón, and M. Yus Tetrahedron Lett. 39 1998 1239 1242
12. For an overview, see: D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 116 2004 286 289
13. For a review on enantioselective reactions promoted by titanium derivatives, see: D.J. Ramón, and M. Yus Recent Res. Devel. Org. Chem. 2 1998 489 523
14. For studies on the mechanism of the enantioselective addition of dialkylzinc to aldehdyes in the presence of titanium alkoxides for the TADDOL ligand, see: D. Seebach, D.A. Plattner, A.K. Beck, Y.M. Wang, D. Hunziker, and W. Petter Helv. Chim. Acta 75 1992 2171 2209
15. Y.N. Ito, X. Ariza, A.K. Beck, A. Boháč, C. Ganter, R.E. Gawley, F.N.M. Kühnle, J. Tuleja, Y.M. Wang, and D. Seebach Helv. Chim. Acta 77 1994 2071 2110
16. D. Weber, and D. Seebach Tetrahedron 50 1994 7473 7484
17. For the BINOL ligand J. Balsells, T.J. Davis, P. Carroll, and P.J. Walsh J. Am. Chem. Soc. 124 2002 10336 10348
18. For hydroxysulfonamide ligands: K.-H. Wu, and H.-M. Gau Organometallics 23 2004 580 588
19. D.J. Ramón, and M. Yus Tetrahedron 54 1998 5651 5666
20. For a review, see: J.-A. Ma, and D. Cahard Angew. Chem., Int. Ed. 43 2004 4566 4583
21. D.J. Ramón, G. Guillena, and D. Seebach Helv. Chim. Acta 79 1996 875 894
22. M.D. Mackey, and J.M. Goodman Chem. Commun. 1997 2383 2384
23. M. Yus, D.J. Ramón, and O. Prieto Tetrahedron: Asymmetry 14 2003 1103 1114
24. M. Yus, D.J. Ramón, and O. Prieto Tetrahedron: Asymmetry 13 2002 2291 2293
25. The ligand HOCSAC was independently and at the same time reported: C. García, L.K. LaRochelle, and P.J. Walsh J. Am. Chem. Soc. 124 2002 10970 10971
26. M. Yus, D.J. Ramón, and O. Prieto Tetrahedron: Asymmetry 13 2002 1573 1579
27. M. Yus, D.J. Ramón, and O. Prieto Eur. J. Org. Chem. 2003 2745 2748
28. O. Prieto, D.J. Ramón, and M. Yus Tetrahedron: Asymmetry 14 2003 1955 1957
29. G. Zanoni, S. Gladiali, A. Marchetti, P. Piccinini, I. Tredici, and G. Vidari Angew. Chem., Int. Ed. 43 2004 846 849
30. G. Fontana, A. Lubineau, and M.-C. Scherrmann Org. Biol. Chem. 3 2005 1375 1380
31. M. Yasuda, K. Hirata, M. Nishino, A. Yamamoto, and A. Baba J. Am. Chem. Soc. 124 2002 13442 13447
32. For examples on enantioselective alkynylation of ketones using titanium complexes, see: P.G. Cozzi, and S. Alesi Chem. Commun. 2004 2448 2449
33. Y. Zhou, R. Wang, Z. Xu, W. Yan, L. Liu, Y. Kang, and Z. Han Org. Lett. 6 2004 4147 4149
34. For examples on hydrozirconation, followed by transmetallation and enantioselective additions, see: P. Wipf, and S. Ribe J. Org. Chem. 63 1998 6454 6455
35. H. Li, and P.J. Walsh J. Am. Chem. Soc. 127 2005 8355 8361
36. For examples on enantioselective phenylation of aldehydes after boron/zinc transmetallation, see: J. Rudolph, F. Schmidt, and C. Bolm Adv. Synth. Catal. 346 2004 867 872
37. J. Rudolph, N. Hermanns, and C. Bolm J. Org. Chem. 69 2004 3997 4000
38. C. Bolm, L. Zani, J. Rudolph, and I. Schiffers Synthesis 2004 2173 2180
39. C. Bolm, F. Schmidt, and L. Zani Tetrahedron: Asymmetry 16 2005 1367 1376
40. S. Özçubukçu, F. Schmidt, and C. Bolm Org. Lett. 7 2005 1407 1409