A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4097-4099

  Le, Julie Cong Dung ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; LIGAND; PYRUVIC ACID;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CRYSTALLIZATION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; MICHAEL ADDITION; SUBSTITUTION REACTION;

ALDEHYDES; CATALYSIS; CHLORIDES; COPPER; ESTERS; GLYOXYLATES; HYDROCARBONS, AROMATIC; LIGANDS; MESYLATES; MOLECULAR STRUCTURE; OXAZOLES; PYRUVATES; SILANES; STEREOISOMERISM;

EID: 8744245317     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048179w     Document Type: Article

References (45)

1. For recent examples of nonaldol approaches, see: Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538-6539. (b) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911. (c) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900-9901. (d) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544-9545. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6196. (g) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699. (h) Tietze, L. F.; Volkel, L.; Wulff, C.; Weigand, B.; Bittner, C.; McGrath, P.; Johnson, K.; Schafer, M. Chem. Eur. J. 2001, 7, 1304-1308. (i) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445-446.
2. For recent examples of nonaldol approaches, see: Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538-6539. (b) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911. (c) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900-9901. (d) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544-9545. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6196. (g) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699. (h) Tietze, L. F.; Volkel, L.; Wulff, C.; Weigand, B.; Bittner, C.; McGrath, P.; Johnson, K.; Schafer, M. Chem. Eur. J. 2001, 7, 1304-1308. (i) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445-446.
3. For recent examples of nonaldol approaches, see: Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538-6539. (b) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911. (c) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900-9901. (d) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544-9545. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6196. (g) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699. (h) Tietze, L. F.; Volkel, L.; Wulff, C.; Weigand, B.; Bittner, C.; McGrath, P.; Johnson, K.; Schafer, M. Chem. Eur. J. 2001, 7, 1304-1308. (i) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445-446.
4. For recent examples of nonaldol approaches, see: Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 6538-6539. (b) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910-8911. (c) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900-9901. (d) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544-9545. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195-6196. (g) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699. (h) Tietze, L. F.; Volkel, L.; Wulff, C.; Weigand, B.; Bittner, C.; McGrath, P.; Johnson, K.; Schafer, M. Chem. Eur. J. 2001, 7, 1304-1308. (i) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445-446.
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