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Volumn 52, Issue 15, 1996, Pages 5263-5301

Diastereofacial selection in nucleophilic additions to unsymmetrically substituted trigonal carbons

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; ORGANIC COMPOUND; PYRAN DERIVATIVE; PYRIDINE DERIVATIVE;

EID: 0029936615     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01023-8     Document Type: Review
Times cited : (114)

References (100)
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    • (1968) Tetrahedron Lett. , vol.2205
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    • Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205; 1971, 383. Cherest, M.; Felkin, H.; Frajerman, C. Tetrahedron Lett. 1971, 379.
    • (1971) Tetrahedron Lett. , pp. 383
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    • For a review, see: Reetz, M.T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569. See also: Fujita, (get Reference 58 from JACS 1991, 113, 5025).
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    • Reetz, M.T.1
  • 22
    • 0010771837 scopus 로고
    • get Reference 58 from
    • For a review, see: Reetz, M.T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569. See also: Fujita, (get Reference 58 from JACS 1991, 113, 5025).
    • (1991) JACS , vol.113 , pp. 5025
    • Fujita1
  • 29
    • 85030191323 scopus 로고    scopus 로고
    • note
    • In a private communication, Professor Houk has provided the following comments concerning microscopic reversibility and transition states of nucleophilic additions. (1) About microscopic reversibility: "Marcus theory is one elegant way to talk about the fact that both thermodynamic factors (heats of reaction) and transition state stabilization are involved in determining activation energies. Microscopic reversibility does not require both forward and reverse rates to be accelerated by a substituent effect, unless the heat of reaction is constant. The lone pair of an oxygen speeds up formation of a cation at an adjacent center, but it also slows down the reverse reaction, because a cation is more stabilized by the lone pair donation than the transition state." (2) About transition states of nucleophilic additions: " - that electron donors slow down nucleophilic additions is ample proof that the transition states are electron rich with respect to reactants. Cieplak model would predict that amides react fastest, then esters, then ketones, then aldehydes, which is wrong."
  • 34
    • 0012892735 scopus 로고
    • (c) For other studies related to the Baker-Nathan order problem, see also: Brown, H. C.; Periasamy, M.; Perumal, P. T. J. Org. Chem. 1984, 49, 2754. Edlund, U. Org. Magn. Reson. 1978, 11, 516. Coney, B. T.; Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1984) J. Org. Chem. , vol.49 , pp. 2754
    • Brown, H.C.1    Periasamy, M.2    Perumal, P.T.3
  • 35
    • 84986792430 scopus 로고
    • (c) For other studies related to the Baker-Nathan order problem, see also: Brown, H. C.; Periasamy, M.; Perumal, P. T. J. Org. Chem. 1984, 49, 2754. Edlund, U. Org. Magn. Reson. 1978, 11, 516. Coney, B. T.; Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1978) Org. Magn. Reson. , vol.11 , pp. 516
    • Edlund, U.1
  • 36
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    • (c) For other studies related to the Baker-Nathan order problem, see also: Brown, H. C.; Periasamy, M.; Perumal, P. T. J. Org. Chem. 1984, 49, 2754. Edlund, U. Org. Magn. Reson. 1978, 11, 516. Coney, B. T.; Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1987) Aust. J. Chem. , vol.40 , pp. 1537
    • Coney, B.T.1    Happer, D.A.R.2
  • 43
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    • (c) Yoshikawa, K.; Hashimoto, M.; Morishima, L. J. Am. Chem. Soc. 1974, 96, 288. Levy, G.; De Loth, P. C. R. Acad. Sci. Ser. C 1974, 279C, 331.
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  • 92
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    • For an excellent review, see: Seeman, J. I. Chem. Rev. 1983, 83, 83.
    • (1983) Chem. Rev. , vol.83 , pp. 83
    • Seeman, J.I.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.