Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3741-3743

  Imbriglio, Jason E ^a   Vasbinder, Melissa M ^a   Miller, Scott J ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 BUTEN 2 ONE; 3-BUTEN-2-ONE; ALDEHYDE; ALKANONE; AMINO ACID; PEPTIDE; PROLINE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMISTRY; ENANTIOSELECTIVITY; HILL REACTION; REACTION ANALYSIS; STEREOISOMERISM;

ALDEHYDES; BUTANONES; CATALYSIS; PEPTIDES; PROLINE; STEREOISOMERISM;

EID: 0142042898     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035466b     Document Type: Article

References (21)

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11. For example: (a) Acylation: Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502. (b) Phosphorylation: Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653-11656. (c) Azidation: Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136. (d) For a review, see: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
12. For example: (a) Acylation: Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502. (b) Phosphorylation: Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653-11656. (c) Azidation: Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136. (d) For a review, see: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
13. For example: (a) Acylation: Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502. (b) Phosphorylation: Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653-11656. (c) Azidation: Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136. (d) For a review, see: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
14. For example: (a) Acylation: Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502. (b) Phosphorylation: Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653-11656. (c) Azidation: Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136. (d) For a review, see: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
15. Shi, M.; Jiang, J.-K.; Li, C.-Q. Tetrahedron Lett. 2002, 43, 127-130.
16. Not all of the peptides screened are shown in Table 1. A representative set for each chain length was prepared.
17. 3 (2:1) solvent mixture.
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19. (b) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479, and references therein.
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