Chiral palladium(II)-catalyzed asymmetric glyoxylate-ene reaction: Alternative approach to the enantioselective synthesis of α-hydroxy esters

Organic Letters

Volumn 2, Issue 25, 2000, Pages 4059-4062

  Hao, Jian ^a   Hatano, Manabu ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000964552     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0066983     Document Type: Article

References (21)

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4. (d) Snider, B. B. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, pp 1-27.
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13. For our highly enantioselective ene-type cyclizations catalyzed by chiral palladium complexes bearing BINAP derivatives, see: Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. In press.
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15. 2: (a) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023.
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18. 2Cl was added 0.5 mmol of olefin 3 and 0.25 mmol of ethyl glyoxylate 4 in 4 mL of toluene at room temperature under an atmosphere of argon. This yellow solution was then stirred at 60 °C for 4 h (reaction was monitored by TLC, AcOEt/hexane = 1/2), solvent was removed in vacuo, and the residue was purified by column chromatography (AcOEt/ hexane = 1/3) to afford a-hydroxy ester (5) as colorless oil.
19. Recently, Evans D. A. et al reported the first example using chiral box copper(II) complexes for catalytic enantioselective carbonyl-ene reactions with monosubstituted olefins in up to 98% ee: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335.
20. (b) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943.
21. (c) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825.