Gram-scale preparation of VAPOL hydrogenphosphate: A structurally distinct chiral brønsted acid

Synthesis

Volumn , Issue 12, 2010, Pages 2106-2109

  Desai, Aman A ^a   Huang, Li ^a   Wulff, William D ^a   Rowland, Gerald B ^b   Antilla, Jon C ^b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Asymmetric catalysis; Br nsted acid; Ligands; Phosphoric acid; VAPOL

Indexed keywords

ASYMMETRIC CATALYSIS; GRAM-SCALE SYNTHESIS; HIGH YIELD; HYDROGEN PHOSPHATES; STARTING MATERIALS;

CATALYSIS; LIGANDS; PHOSPHORIC ACID; SYNTHESIS (CHEMICAL);

ACIDS;

BRONSTED ACID; PHOSPHORIC ACID DERIVATIVE;

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR DOCKING; REACTION ANALYSIS; REPRODUCIBILITY; SHORT SURVEY;

EID: 77953273372     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218783     Document Type: Short Survey

References (34)

1. Bao J, Wulff W D., Rheingold A L., J. Am. Chem. Soc. 1993 115 3814
2. Antilla J C., Wulff W D., J. Am. Chem. Soc. 1999 121 5099
3. Antilla J C., Wulff W D., Angew. Chem. Int. Ed. 2000 39 4518
4. Loncaric C, Wulff W D., Org. Lett. 2001 3 3675
5. Patwardhan A P., Pulgam V R., Zhang Y, Wulff W D., Angew. Chem. Int. Ed. 2005 44 6169
6. Deng Y, Lee Y R., Newman C A., Wulff W D., Eur. J. Org. Chem. 2007 2068
7. Lu Z, Zhang Y, Wulff W D., J. Am. Chem. Soc. 2007 129 7185
8. Newman C, Antilla J C., Chen P, Predeus A, Fielding L, Wulff W D., J. Am. Chem. Soc. 2007 129 7216
9. Zhang Y, Desai A, Lu Z, Hu G, Ding Z, Wulff W D., Chem. Eur. J. 2008 14 3785
10. Zhang Y, Lu Z, Desai A, Wulff W D., Org. Lett. 2008 10 5429
11. Zhang Y, Lu Z, Wulff W D., Synlett 2009 2715
12. Bao J, Wulff W D., Tetrahedron Lett. 1995 36 3321
13. Heller D P., Goldberg D R., Wulff W D., J. Am. Chem. Soc. 1997 119 10551
14. Xue S, Yu S, Deng Y, Wulff W D., Angew. Chem. Int. Ed. 2001 40 2271
15. Bolm C, Frison J.-C, Zhang Y, Wulff W D., Synlett 2004 1619
16. Heller D P., Goldberg D R., Wu H, Wulff W D., Can. J. Chem. 2006 84 1487
17. Lou S, Schaus S E., J. Am. Chem. Soc. 2008 130 6922
18. For the synthesis of VAPOL and VANOL, see:, Bao J, Wulff W D., Dominy J B., Fumo M J., Grant E B., Rob A C., Whitcomb M C., Yeung S M., Ostrander R L., Rheingold A L., J. Am. Chem. Soc. 1996 118 3392
19. Akiyama T, Itoh J, Yokota K, Fuchibe K, Angew. Chem. Int. Ed. 2004 43 1566
20. Uraguchi D, Terada M, J. Am. Chem. Soc. 2004 126 5356
21. For reviews on chiral phosphoric acid catalysis, see:, Akiyama T, Itoh J, Fuchibe K, Adv. Synth. Catal. 2006 348 999
22. Connon S J., Angew. Chem. Int. Ed. 2006 45 3909
23. Akiyama T, Chem. Rev. 2007 107 5744
24. Terada M, Chem. Commun. 2008 4097
25. Rowland G B., Zhang H, Rowland E B., Chennamadhavuni S, Wang Y, Antilla J C., J. Am. Chem. Soc. 2005 127 15696
26. Li G, Liang Y, Antilla J C., J. Am. Chem. Soc. 2007 129 5830
27. For theoretical modeling of the chiral phosphoric acid mediated reductions with Hantzschs ester, see:, Simon L, Goodman J M., J. Am. Chem. Soc. 2008 130 8741
28. Liang Y, Rowland E B., Rowland G B., Perman J A., Antilla J C., Chem. Commun. 2007 4477
29. Rowland E B., Rowland G B., Rivera-Otero E, Antilla J C., J. Am. Chem. Soc. 2007 129 12084
30. DellaSala G, Lattanzi A, Org. Lett. 2009 11 3330
31. Larson S E., Baso J C., Li G, Antilla J C., Org. Lett. 2009 11 5186
32. Li G, Antilla J C., Org. Lett. 2009 11 1075
33. Li G, Fronczek F R., Antilla J C., J. Am. Chem. Soc. 2008 130 12216
34. Li G, Rowland G B., Rowland E B., Antilla J C., Org. Lett. 2007 9 4065