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4
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0001266662
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For a discussion of the potential benefits of 5,5-dimethyloxazolidin-2- ones (SuperQuats) see: a) S. D. Bull, S. G. Davies, S. Jones, H. J. Sanganee, J. Chem. Soc. Perkin Trans. 1 1999, 387-398;
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For a discussion of the potential benefits of 5,5-dimethyloxazolidin-2- ones (SuperQuats) see: a) S. D. Bull, S. G. Davies, S. Jones, H. J. Sanganee, J. Chem. Soc. Perkin Trans. 1 1999, 387-398;
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5
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c) S. D. Bull, S. G. Davies, R. L. Nicholson, H. J. Sanganee, A. D. Smith, Tetrahedron: Asymmetry 2000, 11, 3475-3479;
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8
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0042735337
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syn-Aldols 6 and 8 were prepared using our previously reported protocols, see: a F. J. P. Feuillet, D. E. J. E. Robinson, S. D. Bull, Chem. Commun. 2003, 2184-2185;
-
syn-Aldols 6 and 8 were prepared using our previously reported protocols, see: a) F. J. P. Feuillet, D. E. J. E. Robinson, S. D. Bull, Chem. Commun. 2003, 2184-2185;
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-
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9
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24144489440
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b) F. J. P. Feuillet, M. Cheeseman, M. F. Mahon, S. D. Bull, Org. Biomol. Chem. 2005, 2976-2989;
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Bull, S.D.4
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10
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18744393478
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c) F. J. P. Feuillet, D. G. Niyadurupola, R. Green, M. Cheeseman, S. D. Bull, Synlett 2005, 1090-1094.
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Feuillet, F.J.P.1
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Bull, S.D.5
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13
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-
36348982982
-
-
[6]).
-
[6]).
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-
-
-
14
-
-
36348937526
-
-
[6]).
-
[6]).
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-
-
-
15
-
-
36348966277
-
-
4 stereocentres of all (4S)- and (4R)-aldols were assigned from the sign of the specific rotation of the (R)- or (S)-α-methyloctanal (14) generated from their retro-aldol cleavage, as well as from the identity of the major imidazolidine diastereoisomer formed from its derivatization with (S,S)-DMPEDA.
-
4 stereocentres of all (4S)- and (4R)-aldols were assigned from the sign of the specific rotation of the (R)- or (S)-α-methyloctanal (14) generated from their retro-aldol cleavage, as well as from the identity of the major imidazolidine diastereoisomer formed from its derivatization with (S,S)-DMPEDA.
-
-
-
-
17
-
-
0037160423
-
-
anti-Aldols 10 and 12 were prepared according to the protocol previously described by D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392-393.
-
anti-Aldols 10 and 12 were prepared according to the protocol previously described by D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392-393.
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18
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0000209750
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84982361666
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For previous reports on the asymmetric syntheses of (S)- or (R)-α-methyloctanal in varying ee values, see: a) G. Consiglio, C. Botteghi, C. Salomon, P. Pino, Angew. Chem. Int. Ed. Engl. 1973, 12, 669-670;
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For previous reports on the asymmetric syntheses of (S)- or (R)-α-methyloctanal in varying ee values, see: a) G. Consiglio, C. Botteghi, C. Salomon, P. Pino, Angew. Chem. Int. Ed. Engl. 1973, 12, 669-670;
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84987455893
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e) K. Maruoka, S. Nakai, M. Sakurai, H. Yamamoto, Synthesis 1986, 130-132;
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27
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36348973147
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The enantiomeric excesses of (R)- and (S)-α- methyloctanal (14) produced in these retro-aldol reactions were determined by derivatisation with (S,S)-DMEPDA.
-
The enantiomeric excesses of (R)- and (S)-α- methyloctanal (14) produced in these retro-aldol reactions were determined by derivatisation with (S,S)-DMEPDA.
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29
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84981810942
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b) D. Seebach, D. Steinmuller, F. Demuth, Angew. Chem. Int. Ed. 1968, 7, 620-621.
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26844459934
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For related Wittig homologations of masked aldehyde equivalents see: a
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For related Wittig homologations of masked aldehyde equivalents see: a) D. J. Dixon, M. S. Scott, C. A. Luckhurst, Synlett 2005, 2420-2424;
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32
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0010419553
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Although the α,β-unsaturated ester (E,R)-18 has not been reported previously, Wittig homologation of related chiral α-alkyl aldehydes are known to proceed with no loss of enantiopurity; See: a) R. Baker, J. C. Head, C. J. Swain, J. Chem. Soc. Perkin Trans. 1 1988, 85-97;
-
Although the α,β-unsaturated ester (E,R)-18 has not been reported previously, Wittig homologation of related chiral α-alkyl aldehydes are known to proceed with no loss of enantiopurity; See: a) R. Baker, J. C. Head, C. J. Swain, J. Chem. Soc. Perkin Trans. 1 1988, 85-97;
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33
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0032538014
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3); See: A. G. Jamieson, A. Sutherland, Org. Biomol. Chem. 2005, 3, 735-736.
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