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Volumn , Issue 8, 2009, Pages 1189-1207

The catalytic asymmetric intramolecular Stetter reaction

Author keywords

Asymmetric synthesis; Benzoin reaction; Carbene catalysis; Nucleophilic catalysis; Organocatalysis; Quaternary stereocenters; Stetter reaction; Triazolium salts

Indexed keywords

ALDEHYDE; BENZOIN; CARBENE; HETEROCYCLIC COMPOUND; NUCLEOPHILE; PHENYLALANINE;

EID: 67649363846     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216654     Document Type: Review
Times cited : (146)

References (104)
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    • For examples of the benzoin reaction that are not referenced later in the text, see
    • For examples of the benzoin reaction that are not referenced later in the text, see: (a) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
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    • For examples of the benzoin reaction with acylsilanes, see
    • (b) For examples of the benzoin reaction with acylsilanes, see: Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463.
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    • For the mechanism of the thiamine-catalyzed benzoin reaction, see: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
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    • Addition of Acyl Carbanion Equivalents to Carbonyl Groups and Enones
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    • (a) Enders, D.; Breuer, K. Addition of Acyl Carbanion Equivalents to Carbonyl Groups and Enones, In Comprehensive Asymmetric Catalysis I-III, Vol.3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 1093.
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    • For related examples of acylsilanes in the Stetter reaction, see
    • For related examples of acylsilanes in the Stetter reaction, see: (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
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    • For a seminal example of an intramolecular Stetter reaction, see
    • (b) For a seminal example of an intramolecular Stetter reaction, see: Trost, B. M.; Shuey, C. D.; DiNinno, F.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1284.
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    • note
    • Investigation of the enantioselectivity as a function of conversion revealed that 80 is formed in 80% ee at 10% conversion, with rapid erosion to 50% ee at 30% conversion.
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    • note
    • Similar observations have been noted by Miller and co-workers; see reference 40.
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    • and references cited therein
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    • It is also possible that the α-hydroxy-α-azolium anion adds to the Michael acceptor in concerted fashion, analogous to the reverse-Cope elimination mechanism seen with hydroxylamine additions; see
    • It is also possible that the α-hydroxy-α-azolium anion adds to the Michael acceptor in concerted fashion, analogous to the reverse-Cope elimination mechanism seen with hydroxylamine additions; see: (a) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.