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Volumn 48, Issue 21, 1992, Pages 4439-4458

Diastereofacial selectivity in the aldol reactions of chiral α-methyl aldehydes: a computer modelling approach.

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

EID: 0026643343     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)80452-X     Document Type: Article
Times cited : (55)

References (61)
  • 7
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    • For recent calculations regarding the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds, see
    • (1991) Tetrahedron , vol.47 , pp. 8991
    • Frenking1    Kœhler2    Reetz3
  • 10
    • 0007911997 scopus 로고
    • Stereoselective synthesis of alcohols, XIX. The sense of asymmetric induction on addition to α-chiral aldehydes
    • (1985) Chemische Berichte , vol.118 , pp. 3966
    • Hoffmann1    Weidmann2
  • 12
    • 84873976195 scopus 로고
    • Stereoselective synthesis of alcohols, XXXIV. Towards an understanding of cram/anti-cram selectivity on addition of crotylboronates to α-methylbutyraldehyde
    • (1990) Chemische Berichte , vol.123 , pp. 2387
    • Hoffmann1    Brinkmann2    Frenking3
  • 13
    • 0001065543 scopus 로고
    • Stereoselective synthesis of alcohols, XXXV. Addition ofE- andZ-crotylboronates to chiral α-substituted aldehydes
    • (1990) Chemische Berichte , vol.123 , pp. 2395
    • Brinkmann1    Hoffmann2
  • 32
    • 0022499278 scopus 로고
    • The outcome of this aldol reaction (Anti-Felkin : Felkin 〉 99:1) was analyzed by the authors by comparing transition structures analogous to C (favoured) and A, which they note is destabilized by (+/-) double gauche pentane interactions between the two methyl group.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4603
    • Patel1    VanMiddlesworth2    Donaubauer3    Gannett4    Sih5
  • 39
    • 0000784039 scopus 로고
    • For a list of interesting applications of the (+/-) double gauche pentane interactions to stereochemical control, see, and footnotes 27,28 in that paper.
    • (1991) J. Org. Chem. , vol.56 , pp. 4151
    • Roush1
  • 49
    • 0002704505 scopus 로고
    • A phenyl group can be viewed as less sterically demanding than the smallest alkyl group (methyl). For example, conformational analyses have shown that the preferred conformation of 1-methyl-1-phenylcyclohexane is that in which the phenyl group maintains an axial orientation with an energy difference between the two conformers of about 0.30–0.34 kcal/mol. See
    • (1971) Tetrahedron Lett. , pp. 3259
    • Allinger1    Tribble2
  • 53
    • 0021775497 scopus 로고
    • and references therein. Reactions of the chiral enolate shown in Scheme 9 with achiral aldehydes have been modelled with good reproduction of the experimental results [e. g. reaction of the (S)-(9-BBN)-enolate with propionaldehyde: expt. re-si ratio ≥ 17:1, calcd. re-si ratio 16:1; see ref. 2b].
    • (1985) Angew. Chem.Int. Ed. Engl. , vol.24 , pp. 1
    • Masamune1    Choy2    Petersen3    Sita4
  • 55
    • 84918692849 scopus 로고    scopus 로고
    • BATCHMIN is the non interactive modelling program connected to MacroModel. Version 3.1 was used on a Silicon Graphics Iris workstation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.