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Volumn 75, Issue 3, 2010, Pages 963-965

Asymmetric Mannich reaction of malonates with imines catalyzed by a chiral calcium complex

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; MALONATES; MANNICH REACTIONS;

EID: 75749096767     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902383b     Document Type: Article
Times cited : (53)

References (35)
  • 1
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    • 3rd ed, Cotton, F. A, Wilkinson, G, Gaus, P. L, Eds, Wiley: New York
    • Basic Inorganic Chemistry, 3rd ed.; Cotton, F. A., Wilkinson, G., Gaus, P. L., Eds.; Wiley: New York, 1995.
    • (1995) Basic Inorganic Chemistry
  • 2
    • 13944268229 scopus 로고    scopus 로고
    • Selected examples of nonenantioselective reactions with alkaline earth metal complexes as catalysts: (a) Crimmin, M. R, Casely, I. J, Hill, M. S. J. Am. Chem. Soc. 2005, 2042
    • Selected examples of nonenantioselective reactions with alkaline earth metal complexes as catalysts: (a) Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 2042.
  • 8
    • 0035833107 scopus 로고    scopus 로고
    • Selected examples of enantioselective reactions with chiral alkaline earth metal complexes: Ca catalysts: (a) Suzuki, T.; Yamagiwa, N.; Matsuo, Y.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M.; Noyori, R. Tetrahedron Lett. 2001, 42, 4669.
    • Selected examples of enantioselective reactions with chiral alkaline earth metal complexes: Ca catalysts: (a) Suzuki, T.; Yamagiwa, N.; Matsuo, Y.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M.; Noyori, R. Tetrahedron Lett. 2001, 42, 4669.
  • 19
    • 0000862669 scopus 로고    scopus 로고
    • For reviews on Mannich and asymmetric Mannich reactions see: a
    • For reviews on Mannich and asymmetric Mannich reactions see: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 21
    • 0001059120 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pflatz, A, Yamamoto, H, Eds, Springer: Berlin, Germany
    • (c) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vol. 2, p 923.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 923
    • Denmark, S.E.1    Nicaise, O.J.-C.2
  • 22
    • 33646511310 scopus 로고    scopus 로고
    • Selected examples with organocatalysts in direct addition of malonates to imines: (a) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
    • Selected examples with organocatalysts in direct addition of malonates to imines: (a) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
  • 32
    • 75749155982 scopus 로고    scopus 로고
    • 2, which was found to be efficient as catalyst in the direct addition of malonates to N-Boc imines.
    • 2, which was found to be efficient as catalyst in the direct addition of malonates to N-Boc imines.
  • 33
    • 75749147166 scopus 로고    scopus 로고
    • Previous optimizations revealed that aromatic solvents were the most efficient
    • Previous optimizations revealed that aromatic solvents were the most efficient.
  • 34
    • 0037032312 scopus 로고    scopus 로고
    • For an efficient preparation of N-Boc imines, see: Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964 and ref 6a.
    • For an efficient preparation of N-Boc imines, see: Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964 and ref 6a.
  • 35
    • 75749112676 scopus 로고    scopus 로고
    • Boc was found to be the most efficient N-protecting group under conditions described in Table 2, entry 11. The N-Cbz analogue of 1a furnished the corresponding product in 54% ee.
    • Boc was found to be the most efficient N-protecting group under conditions described in Table 2, entry 11. The N-Cbz analogue of 1a furnished the corresponding product in 54% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.