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51
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78649800766
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We have previously shown that the doubly diastereoselective conjugate addition of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of chiral α,β-unsaturated carbonyl compounds proceeds under the dominant stereocontrol of the lithium amide, for instance see
-
We have previously shown that the doubly diastereoselective conjugate addition of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of chiral α,β-unsaturated carbonyl compounds proceeds under the dominant stereocontrol of the lithium amide, for instance see
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-
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53
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77956264668
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S.G. Davies, A.M. Fletcher, G.J. Hermann, G. Poce, P.M. Roberts, A.D. Smith, M.J. Sweet, and J.E. Thomson Tetrahedron: Asymmetry 21 2010 1635 See also Ref. 15d
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(2010)
Tetrahedron: Asymmetry
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, pp. 1635
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Davies, S.G.1
Fletcher, A.M.2
Hermann, G.J.3
Poce, G.4
Roberts, P.M.5
Smith, A.D.6
Sweet, M.J.7
Thomson, J.E.8
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0021775497
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For reviews concerning the phenomenon of double asymmetric induction, see: S. Masamune, W. Choy, J.S. Petersen, and L.R. Sita Angew. Chem., Int. Ed. Engl. 24 1985 1
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Masamune, S.1
Choy, W.2
Petersen, J.S.3
Sita, L.R.4
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56
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17444396764
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For the utility of 3-pentyl esters in synthesis see, for example: S.G. Davies, D. Díez, S.H. Dominguez, N.M. Garrido, D. Kruchinin, P.D. Price, and A.D. Smith Org. Biomol. Chem. 3 2005 1284
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Davies, S.G.1
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Kruchinin, D.5
Price, P.D.6
Smith, A.D.7
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59
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78649775401
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3)r. The enantiomeric purities of compounds 12 and 21 were inferred from that of (R)-16
-
3). The enantiomeric purities of compounds 12 and 21 were inferred from that of (R)-16.
-
-
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61
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78649777179
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For previous syntheses of epi-negamycin 2, see Refs. 4e,g,5e. For previous syntheses of epi-negamycin trifluoroacetic acid salt 2·TFA, see Ref. 4l
-
For previous syntheses of epi-negamycin 2, see Refs. 4e,g,5e. For previous syntheses of epi-negamycin trifluoroacetic acid salt 2·TFA, see Ref. 4l.
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62
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78649793123
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1H NMR spectra of the crude reaction mixtures and the isolated products precluded a more accurate determination of the reaction diastereoselectivity and/or product diastereoisomeric ratio
-
1H NMR spectra of the crude reaction mixtures and the isolated products precluded a more accurate determination of the reaction diastereoselectivity and/or product diastereoisomeric ratio.
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63
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78649779232
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In the case of the Hegedus synthesis a common intermediate was also derivatised to (+)-negamycin 1, and in the case of the I.C.I. Pharma synthesis the C(3)-stereogenic centre within (-)-5-epi-negamycin 2 was derived from (R)-aspartic acid; their stereochemical assignments are therefore secure
-
In the case of the Hegedus synthesis a common intermediate was also derivatised to (+)-negamycin 1, and in the case of the I.C.I. Pharma synthesis the C(3)-stereogenic centre within (-)-5-epi-negamycin 2 was derived from (R)-aspartic acid; their stereochemical assignments are therefore secure.
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65
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0018967101
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3-Aminopropanamidine dihydrochloride 29·2HCl was prepared in 25% overall yield from commercially available 3-aminopropionitrile fumarate via N-tosyl protection, ethanolysis, treatment with ammonia and deprotection. For a similar procedure, see: A. Pierdet, L. Nédélec, V. Delaroff, and A. Allais Tetrahedron 36 1980 1763
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(1980)
Tetrahedron
, vol.36
, pp. 1763
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Pierdet, A.1
Nédélec, L.2
Delaroff, V.3
Allais, A.4
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66
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5244370033
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A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Organometallics 15 1996 1518
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(1996)
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, vol.15
, pp. 1518
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Pangborn, A.B.1
Giardello, M.A.2
Grubbs, R.H.3
Rosen, R.K.4
Timmers, F.J.5
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71
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1H NMR spectrum of this compound were too broad to be assigned
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1H NMR spectrum of this compound were too broad to be assigned.
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