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Volumn 125, Issue 29, 2003, Pages 8706-8707

Ni(II) Bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates

Author keywords

[No Author keywords available]

Indexed keywords

N PROPIONYLTHIAZOLIDINETHIONE DERIVATIVE; NICKEL BIS(OXAZOLINE); NICKEL COMPLEX; THIAZOLIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 0038298158     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035509j     Document Type: Article
Times cited : (201)

References (25)
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    • (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178. (c) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539-1542.
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    • Under our conditions N-acyloxazolidinones were unreactive
    • For a stoichiometric, Sn(OTt)2/chiral diamine-mediated aldol reaction with theses substrates, see Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1983, 297-300. Under our conditions, N-acyloxazolidinones were unreactive.
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    • note
    • 3.
  • 10
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    • note
    • n. Conversion suffered greatly with <2 equiv of 2.6-lutidine.
  • 11
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    • For examples of Ni(II) complexes in chiral Lewis acid catalysis, see: (a) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356.
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    • For examples of Ni(II) complexes in chiral Lewis acid catalysis, see: (a) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355-12356.
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    • note
    • 2 thus generated in situ be catalytically active.
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    • See Supporting Information for X-ray crystallographic data
    • See Supporting Information for X-ray crystallographic data.
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    • note
    • The anhydrous catalyst was stored in a glovebox. Hydrated catalyst was less effective in aldol reactions. See Supporting Information for X-ray crystallographic data.
  • 17
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    • note
    • With the preformed catalyst, conversion increased by 5% and enantioselectivity by 1-2%.
  • 18
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    • note
    • Suprisingly, enantioselectivity for p-MeOPhCHO was moderate (62%).
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    • note
    • For a similar catalytic cycle, see ref 3b.
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    • note
    • Ancillary ligands are omitted for the sake of clarity. The aldol transition state likely involves a five- or six-coordinate nickel complex.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.