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7
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(b) Evans, D. A.; Urpí, F.; Sommers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
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Bilodeau, M.T.5
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8
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25444529160
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note
-
On the other hand, opening of the lactone ring of 7 with (R,R)-pseudoephedrine and protection/activation of the vicinal diol as a sulfite ester, followed by reaction with 3-methylbutanal (as a model) and tetrahydrofuran ring formation with NaH posed diverse problems, such as a moderate yield of the aldol reaction and no cyclization in the last step. Use of a stronger EWG-sulfate instead of sulfite-posed problems also, i.e., poor yields of the sulfate preparation and a premature elimination reaction.
-
-
-
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9
-
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12644312578
-
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(a) Mancuso, A. J.; Huang, S. L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
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Mancuso, A.J.1
Huang, S.L.2
Swern, D.3
-
12
-
-
0026739942
-
-
Compound (S)-7 is usually obtained through diazotization of L-glutamic acid, lactonization, and reduction of the carboxyl group with borane (or related procedures). See: (a) Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537.
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Tetrahedron: Asymmetry
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Lehmann, J.1
Pieper, B.2
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13
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0026343021
-
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and references therein
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(b) Figadère, B.; Harmange, J.-C.; Laurens, A.; Cavé, A. Tetrahedron Lett. 1991, 32, 7539 and references therein.
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Figadère, B.1
Harmange, J.-C.2
Laurens, A.3
Cavé, A.4
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14
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0000178458
-
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For an alternative synthesis of 6 from D-mannitol, see: (c) Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Tetrahedron 1990, 46, 3667.
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Tetrahedron
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Chattopadhyay, S.1
Mamdapur, V.R.2
Chadha, M.S.3
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15
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0001081620
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Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J. Am. Chem. Soc. 1971, 93, 1379.
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Whitesides, G.M.1
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Krieger, J.K.3
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16
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0001657421
-
-
Conversion of 6 to the corresponding epoxyalcohol with titanium tetraisopropoxide and polymethylhydrosiloxane (Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1995, 60, 7884) was not useful as the 4,5-epoxy-1-pentanol isomerized to 5-hydroxymethyloxolane (THF derivative) under the reaction conditions, as might be expected.
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Reding, M.T.1
Buchwald, S.L.2
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17
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0031006430
-
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For related procedures, see: (a) Nagumo, S.; Furukawa, T.; Ono, M.; Akita, H. Tetrahedron Lett. 1997, 38, 2849.
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Nagumo, S.1
Furukawa, T.2
Ono, M.3
Akita, H.4
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18
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-
0027935856
-
-
(b) Harrowven, D. C.; Dennison, S. T.; Hayward, J. S. Tetrahedron Lett. 1994, 35, 7467.
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Harrowven, D.C.1
Dennison, S.T.2
Hayward, J.S.3
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19
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0001553502
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Lipshutz, B. H.; Koerner, M.; Parker, D. A. Tetrahedron Lett. 1987, 28, 945.
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Lipshutz, B.H.1
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Parker, D.A.3
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20
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-
25444518891
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note
-
4, and finally 1.1 equiv of DIPEA.
-
-
-
-
21
-
-
25444471492
-
-
PhD Thesis, Universitat de Barcelona
-
iPr) afforded a mixture of two aldols: Mas, G. PhD Thesis, Universitat de Barcelona, 2000.
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(2000)
-
-
Mas, G.1
-
22
-
-
25444438951
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-
Master's Thesis, Universitat de Barcelona
-
(c) When parallel aldol-like reactions were carried out in our lab with thiazolidine-2-thione chiral auxiliaries (instead of the oxazolidin-2-one derivatives shown in Schemes 2 and 4), the results were disappointing: Batlle, M. Master's Thesis, Universitat de Barcelona, 2003.
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(2003)
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Batlle, M.1
-
23
-
-
37049091522
-
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For leading references on thiazolidine-2-thione auxiliaries, see: (d) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418.
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J. Chem. Soc., Chem. Commun.
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Nagao, Y.1
Yamada, S.2
Kumagai, T.3
Ochiai, M.4
Fujita, E.5
-
24
-
-
0000665968
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(e) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391 [acetate aldol reactions of Sn(II) enolates].
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Nagao, Y.1
Hagiwara, Y.2
Kumagai, T.3
Ochiai, M.4
Inoue, T.5
Hashimoto, K.6
Fujita, E.7
-
25
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0028862166
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-
and references therein (preparation)
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(f) Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604 and references therein (preparation).
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Delaunay, D.1
Toupet, L.2
Corre, M.L.3
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26
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0030566818
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(g) González, A.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949 (acetate aldol reactions of Ti enolates).
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González, A.1
Aiguadé, J.2
Urpí, F.3
Vilarrasa, J.4
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27
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0030882988
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-
Also see: (h) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883 (Ti enolates of oxazolidine-2-thione derivatives).
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Crimmins, M.T.1
King, B.W.2
Tabet, E.A.3
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0035830561
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(i) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894 and references therein.
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Tabet, E.A.3
Chaudhary, K.4
-
30
-
-
25444504467
-
-
note
-
For the cleavage of the final boron complexes, in all cases the reaction mixtures were quenched at low temperature with MeOH and buffered water (pH 7). The resulting solutions or suspensions were stirred for ca. 12 h (no hydrogen peroxide or bases were added).
-
-
-
-
31
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0344242779
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(a) Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 307.
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Leighton, J.L.3
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33
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-
25444531643
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-
note
-
3H ("Superhydride", 2.2 equiv) in THF at -78°C cleaved exclusively the chiral auxiliary of 11; however, in the case of 23, several products were produced.
-
-
-
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35
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0001539371
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(b) Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697.
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Vilarrasa, J.4
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0001619813
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For the use of the PySe group in syn selenoxide eliminations, see: (c) Toshimitsu, A.; Owada, H.; Terao, K.; Uemura, S.; Okana, M. J. Org. Chem. 1984, 49, 3796.
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(d) Toshimitsu, A.; Hayashi, G.; Terao, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1988, 2113 and references therein.
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