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Volumn 1, Issue 21, 2003, Pages 3811-3819

Reflections on spontaneous asymmetric synthesis by amplifying autocatalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ALKYLATION; CATALYSIS; CATALYSTS; DIMERIZATION; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

EID: 0344981496     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b307382n     Document Type: Article
Times cited : (114)

References (58)
  • 19
    • 0014447324 scopus 로고
    • Oxford University Press, Oxford; ch 7
    • M. Calvin, Chemical Evolution, Oxford University Press, Oxford, 1969, ch 7.
    • (1969) Chemical Evolution
    • Calvin, M.1
  • 23
    • 0037453377 scopus 로고    scopus 로고
    • (b) An essentially similar conclusion concerning the involvement of a homochiral dimer catalyst was subsequently reached in the analysis of autocatalytic reactions caried out at -25°C: I. Sato, D. Omiya, H. Igarashi, K. Kato, Y. Ogi, K. Tsukiyama and K. Soai, Tetrahedron: Asymmetry, 2003, 14, 975-979.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 975-979
    • Sato, I.1    Omiya, D.2    Igarashi, H.3    Kato, K.4    Ogi, Y.5    Tsukiyama, K.6    Soai, K.7
  • 30
    • 0344839091 scopus 로고    scopus 로고
    • note
    • The detailed solution structure of the Zn alkoxide product will be discussed in ensuing publications. For the moment, a racemic sample gives two superposable 1-H NMR spectra corresponding on the one hand to R,S-alkoxide and on the other to R,R- or S,S-alkoxide, exchange being slow on the NMR timescale at ambient temperature. The two may be readily distinguished in the aromatic region around 8.6 ppm, with the racemate at lower field.
  • 31
    • 4243511953 scopus 로고    scopus 로고
    • Blackmond has carried out an extensive study of the precipitation phenomenon under catalytic turnover conditions
    • private communication
    • Professor D. G. Blackmond has carried out an extensive study of the precipitation phenomenon under catalytic turnover conditions; private communication.
    • Professor, D.G.1
  • 32
    • 0344839076 scopus 로고    scopus 로고
    • note
    • 2O results reported in Fig. 3 are 37(R), 20(R) and 90(S) ee.
  • 34
    • 0012789728 scopus 로고
    • This derivation is normally attributed to W. H. Mills, Chem. Ind., 1932, 750, but has a longer history described in Mislow's review (ref. 16).
    • (1932) Chem. Ind. , pp. 750
    • Mills, W.H.1
  • 35
    • 0004216426 scopus 로고
    • Clarendon Press (OUP), Oxford
    • For an interesting discussion see S. F. Mason, Chemical Evolution, Clarendon Press (OUP), Oxford, 1992, pp. 266
    • (1992) Chemical Evolution , pp. 266
    • Mason, S.F.1
  • 36
    • 0036041901 scopus 로고    scopus 로고
    • ff. For a recent formal derivation see: K. Iwamoto, Phys. Chem. Chem. Phys., 2002, 4, 3975-3979 and papers by the author cited therein.
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 3975-3979
    • Iwamoto, K.1
  • 37
    • 0345270418 scopus 로고    scopus 로고
    • note
    • This differs from the interpretation offered in our original paper (ref. 9), but caution is warranted by the fact that DFT calculations indicate that the macrocyclic dimer postulated there is not the lowest energy structure by a significant margin.
  • 38
    • 0344839050 scopus 로고    scopus 로고
    • note
    • Representing an ideal, since the real system will involve continual spontaneous reactions that will diminish in significance as the autocalytic process gradually becomes dominant. The idea that the statistical enantiomeric excess in a stochastic mechanism is dependent on the initial pool provided by the background reaction is implicit in the discussions in ref. 9b and ref. 11.
  • 40
    • 0035263817 scopus 로고    scopus 로고
    • For general reviews of Zn alkylations see: L. Pu and H. B. Yu, Chem. Rev., 2001, 101, 757-824
    • (2001) Chem. Rev. , vol.101 , pp. 757-824
    • Pu, L.1    Yu, H.B.2
  • 56
    • 0344407417 scopus 로고    scopus 로고
    • personal communication
    • P. Knochel, personal communication.
    • Knochel, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.