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Volumn 39, Issue 29, 1998, Pages 5229-5232

2,3-Wittig rearrangement by partial reduction of diallyl acetals with SmI2 in acetonitrile

Author keywords

Acetals; Rearrangement; Reduction; Samarium and compounds

Indexed keywords

ACETAL; ACETONITRILE;

EID: 0032537711     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01028-4     Document Type: Article
Times cited : (15)

References (24)
  • 1
    • 0025787050 scopus 로고
    • 1 For recent reviews on 2,3-Wittig rearrangement, see: Mikami, K.; and Nakai, T. Synthesis 1991, 594. Marshall, J. A. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
    • (1991) Synthesis , pp. 594
    • Mikami, K.1    Nakai, T.2
  • 2
    • 0000535071 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • 1 For recent reviews on 2,3-Wittig rearrangement, see: Mikami, K.; and Nakai, T. Synthesis 1991, 594. Marshall, J. A. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 975-1014
    • Marshall, J.A.1
  • 3
    • 0000135630 scopus 로고
    • 1 For recent reviews on 2,3-Wittig rearrangement, see: Mikami, K.; and Nakai, T. Synthesis 1991, 594. Marshall, J. A. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
    • (1994) Org. React. , vol.46 , pp. 105
    • Nakai, T.1    Mikami, K.2
  • 7
    • 0000273487 scopus 로고
    • 4 Broka C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. Kruse, B.; Brückner, R. Chem. Ber. 1989, 122, 2023.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2981
    • Broka, C.A.1    Shen, T.2
  • 8
    • 0000288344 scopus 로고
    • 4 Broka C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. Kruse, B.; Brückner, R. Chem. Ber. 1989, 122, 2023.
    • (1989) Chem. Ber. , vol.122 , pp. 2023
    • Kruse, B.1    Brückner, R.2
  • 10
    • 0010336911 scopus 로고    scopus 로고
    • 2 because of their instability and inaccessibility
    • 2 because of their instability and inaccessibility.
  • 11
    • 1542635426 scopus 로고    scopus 로고
    • 2O or TFA to give the corresponding methyl ethers, see; Studer A.; Curran, D. P. Synlett 1996, 255.
    • (1996) Synlett , pp. 255
    • Studer, A.1    Curran, D.P.2
  • 12
    • 0013939727 scopus 로고
    • 8 Acetals were prepared by literature procedures. For 1a-1d: House, H. O.; Latham, R. A.; Slater, C. D. J. Org. Chem. 1966, 31, 2667. For 1e: Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
    • (1966) J. Org. Chem. , vol.31 , pp. 2667
    • House, H.O.1    Latham, R.A.2    Slater, C.D.3
  • 13
    • 0000169587 scopus 로고
    • 8 Acetals were prepared by literature procedures. For 1a-1d: House, H. O.; Latham, R. A.; Slater, C. D. J. Org. Chem. 1966, 31, 2667. For 1e: Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1357
    • Tsunoda, T.1    Suzuki, M.2    Noyori, R.3
  • 19
    • 33845550583 scopus 로고
    • 12 It has been shown that Z-form of benzyl crotyl ether exhibits a high erythro selectivity whereas E-form shows a low threo or sometimes the opposite sense of diastereoselectivity in base-deprotonation, see: Mikami, K.; Kimura, Y.; Kishi, N.; Nakai, T. J. Org. Chem. 1983, 48, 279.
    • (1983) J. Org. Chem. , vol.48 , pp. 279
    • Mikami, K.1    Kimura, Y.2    Kishi, N.3    Nakai, T.4
  • 20
    • 0010416519 scopus 로고    scopus 로고
    • 7 Thus, we believe to be difficult to reduce aliphatic acetals without any additives
    • 7 Thus, we believe to be difficult to reduce aliphatic acetals without any additives.
  • 22
    • 0000870358 scopus 로고
    • 15 There is a example where HMPA serves to slow down the reaction rate by strong coordination to a metal, see: Lefour, J.-M.; Loupy, A. Tetrahedron 1978, 34, 2597.
    • (1978) Tetrahedron , vol.34 , pp. 2597
    • Lefour, J.-M.1    Loupy, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.