Asymmetric epoxidation of α,β-unsaturated ketones under phase-transfer catalyzed conditions

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7563-7566

  Arai, Shigeru ^a   Tsuge, Hiroki ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Asymmetric reactions; Catalysts; Epoxidation; Phase transfer

Indexed keywords

BROMINE DERIVATIVE; CHALCONE; CINCHONINE; HYDROGEN PEROXIDE; KETONE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; EPOXIDATION;

EID: 0032497664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01646-3     Document Type: Article

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22. 10. A part of this work was presented at the 1997 International Phase-Transfer Catalysis Conference held in Nagoya, Japan, on September 24-27, 1997: Tsuge, H.; Arai, S.; T. Shioiri, Abstracts of Papers, p. 87.
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31. 13. Purchased from Aldrich Chemical Co., Ltd.
32. 14. Using a stronger base such as NaOH or KOH instead of LiOH gave the 2a with a slightly lower ee in this reaction system.
33. 3, alkyl groups induced derivatives, or regioisomers of 4-iodo derivatives such as 2-iodo or 3-iodo ones were less effective in this reaction system and afforded the desired products with lower ee.
34. 2O: C, 52.02; H, 4.87; N, 4.67. Found: C, 51.96; H, 5.16; N, 4.61. According to this procedure, the other PTCs described in Table 1 can be easily prepared.
35. 4. Removal of the solvent followed by flash column chromatography (silica gel, hexane:diethyl ether = 9:1) gave the desired product 2d as a colorless solid (238.3 mg, quantitative, 92% ee). Enantiomeric excess was determined by HPLC analysis using DAICEL CHIRALCEL AD, hexane:i-PrOH = 50:1, flow rate:1.0 mL/min. The retention time was 19.0 min for the (αS,βR)-isomer and 25.1 min for the (αR,βS)-isomer, with detection at 254 nm.
36. 18. Chloroform gave the best results using the β-alkyl enones as substrates except for 1 g.
37. 12a PTC H and I were easily prepared from the corresponding ammonium salt.