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Published TCIMAIL newest issue No.199
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Useful Chiral Dirhodium(II) Complex Catalyst
No.144(March 2011)
- T2658
- Tetrakis[N-tetrachlorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct (1a)
- T2659
- Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct (1b)
- T2660
- Tetrakis[N-tetrafluorophthaloyl-(R)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct (2a) (*This product is discontinued.)
- T2661
- Tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinato]dirhodium Bis(ethyl Acetate) Adduct (2b)
Hashimoto et al. have developed chiral dirhodium(II) complexes,
Rh2(R-PTTL)4, Rh2(S-PTTL)4,
Rh2(R-TCPTTL)4, Rh2(S-TCPTTL)4,
Rh2(R-TFPTTL)4 and Rh2(S-TFPTTL)4, and reported their
usefulness. According to their results, intramolecular C-H insertion reactions, 1,3-dipolar cycloaddition of
carbonyl ylides and amination of silyl enol ethers are catalyzed by these dirhodium(II) complexes to proceed
highly enantioselectively and give corresponding products in high yields.
Typical Procedure: 1)
A solution of diazo compound 3 (60.5 mg, 0.20 mmol) and styrene (62.5 mg, 0.60 mmol) in CF3C6H5 (1.0 mL) is added via syringe pump over 1 h to a stirred solution of 1b (3.95 mg, 0.002 mmol, 1 mol%) in CF3C6H5 (1.0 mL). After complete addition, the reaction mixture is concentrated in vacuo, and the residue is purified by column chromatography (silica gel, hexane:EtOAc = 6:1) to provide 4 (64.5 mg, Y. 85%) as a white solid.
A solution of diazo compound 3 (60.5 mg, 0.20 mmol) and styrene (62.5 mg, 0.60 mmol) in CF3C6H5 (1.0 mL) is added via syringe pump over 1 h to a stirred solution of 1b (3.95 mg, 0.002 mmol, 1 mol%) in CF3C6H5 (1.0 mL). After complete addition, the reaction mixture is concentrated in vacuo, and the residue is purified by column chromatography (silica gel, hexane:EtOAc = 6:1) to provide 4 (64.5 mg, Y. 85%) as a white solid.
References
- 1) Enantioselective 1,3-dipolar cycloaddition of carbonyl ylide
- 2) Enantioselective amination of silyl enol ether
Related Compounds
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