Control of up to five stereocenters in a cascade reaction: Synthesis of highly functionalized five-membered rings

Journal of the American Chemical Society

Volumn 130, Issue 23, 2008, Pages 7194-7195

  Li, Hao ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MOLECULE; MUKAIYAMA REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 44949109287     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801488z     Document Type: Article

References (12)

1. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186.
2. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354-366.
3. Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
4. Enders, D.; Huttl, M. R. M.; Grondal, C. Nature 2006, 441, 861-863.
5. Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604-1606.
6. Zu, L.; Li, H.; Xie, H.; Wang, J.; Jiang, W.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732-3734.
7. Mukaiyama-Aldol-Prins cyclization cascade reaction (MAP) was put forward firstly by Rychnovsky and successfully applied to construct a THP ring. Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420-8421.
8. Balme, G.; Gore, J. J. Org. Chem. 1983, 48, 3336-3338.
9. Chan, K. P.; Loh, T. P. Org. Lett. 2005, 7, 4491-4494.
10. Liu, F.; Loh, T. P. Org. Lett. 2007, 9, 2063-2066.
11. Zhao, Y. J.; Chng, S. S.; Loh, T. P. J. Am. Chem. Soc. 2007, 129, 492-493.
12. Johnson, W. S.; Harbert, C. A.; Ratcliffe, B. E.; Stipanovic, R. D. J. Am. Chem. Soc. 1976, 98, 6188-6193.