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Volumn 53, Issue 48, 1997, Pages 16213-16228

trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of α-hydroxy- carboxylic acids, esters, amides and ketones

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIANE 1,3 DIOXIDE; 2 HYDROXYCARBOXYLIC ACID ESTER; 3,4 DIHYDROXYMANDELIC ACID; AMIDE; ANION; BENZALDEHYDE; CARBOXYLIC ACID DERIVATIVE; COPPER DERIVATIVE; ESTER; KETONE; OXIDE; S ETHYL ALPHA HYDROXYTHIOESTER; THIOESTER; UNCLASSIFIED DRUG;

EID: 0030831046     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01010-7     Document Type: Conference Paper
Times cited : (52)

References (51)
  • 2
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    • Heathcock, C. H. in Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3, part B.
    • (1984) Asymmetric Synthesis , vol.3 , Issue.PART B
    • Heathcock, C.H.1
  • 16
    • 0001272894 scopus 로고
    • L. O. Paquette, Ed.; Wiley: New York
    • For an excellent review see: de Lucchi, O. In Organic Reactions; L. O. Paquette, Ed.; Wiley: New York, 1991; Vol. 40; pp 157-405.
    • (1991) Organic Reactions , vol.40 , pp. 157-405
    • De Lucchi, O.1
  • 17
    • 0001100617 scopus 로고
    • The conditions used for the Pummerer reaction were taken from work by Hirama et al: Hirama, M.; Hioki, H.; Ito, S. Tetrahedron.Lett. 1988, 29, 3125-3128.
    • (1988) Tetrahedron. Lett. , vol.29 , pp. 3125-3128
    • Hirama, M.1    Hioki, H.2    Ito, S.3
  • 19
    • 0001595852 scopus 로고
    • For an excellent review on trans-esterification see: Otera, J. Chem. Rev. 1993, 93, 1449-1470. As far as we are aware trans-thiolesterification has not been carried out before.
    • (1993) Chem. Rev. , vol.93 , pp. 1449-1470
    • Otera, J.1
  • 20
    • 0025328745 scopus 로고
    • These conditions were also used to convert Evans' oxazolidinone to the thioester in particularly hindered substrates: (a) Damon, R. E.; Coppola, G. M. Tetrahedron Lett. 1990, 31, 2849-2852.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2849-2852
    • Damon, R.E.1    Coppola, G.M.2
  • 22
    • 0342931213 scopus 로고    scopus 로고
    • All ee measurements were conducted on THP deprotected compound 15a using chiral HPLC
    • All ee measurements were conducted on THP deprotected compound 15a using chiral HPLC.
  • 34
    • 0001597804 scopus 로고
    • Basic hydrogen peroxide has been used to hydrolyse Evans' oxazolidinone: Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144. Thioesters are not as easily hydrolysed as is commonly believed. For kinetic studies see ref. 26.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6141-6144
    • Evans, D.A.1    Britton, T.C.2    Ellman, J.A.3
  • 45
    • 0343366529 scopus 로고    scopus 로고
    • note
    • We also noted that the diastereomeric ratio of recovered starting material 10a (Fe(acac)3-reaction; cuprate addition at -78 °C as well as of ketone 27a had changed in the presence of the Grignard reagent. Apparently Lewis-acidic magnesium compounds catalyse the opening and closing of the THP acetal which leads to the observed partial isomerisation.


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