Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors

Tetrahedron

Volumn 62, Issue 28, 2006, Pages 6630-6639

  Matsunaga, Shigeki ^a   Qin, Hongbo ^a   Sugita, Mari ^a   Okada, Shigemitsu ^a   Kinoshita, Tomofumi ^a   Yamagiwa, Noriyuki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CUMENE HYDROPEROXIDE; ESTER; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 33744782373     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.074     Document Type: Article

References (48)

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39. For the use of N-acylpyrrole as a donor in direct Mannich-type reaction, see:. Harada S., Handa S., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 44 (2005) 4365
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44. 3 was purchased from Kojundo Chemical Laboratory Co., Ltd (fax: +81 492 84 1351; e-mail: sales@kojundo.co.jp).
45. Reaction rate tendency: chalcone>N-acylpyrrole 1a>benzalacetone. N-Acylpyrrole 1a had slightly lower reactivity than chalcone, and showed slightly higher reactivity than benzalacetone.
46. 8-BINOL, see:. Terry T.-L.A.-Y., Chan S.-S., and Chan A.S.C. Adv. Synth. Catal. 345 (2003) 537
47. The present catalysis is applicable to various α,β-unsaturated N-acylpyrroles shown in Tables 1 and 2 to give epoxides in good yield and ee, except for 1m and 1n. Epoxidation of α,β-unsaturated N-acylpyrroles 1m and 1n did not proceed due to steric hindrance.
48. N-Acylpyrrole unit can also be transformed into ethyl ester in good yield by treatment with either EtSLi in EtOH or NaOEt in EtOH. See, Refs. 7, 9, and 10.