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(h) In Ref. 1f and 181-238
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(h) Heathcock, C.H. In Ref. 1f, pp 133-179 and 181-238.
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Heathcock, C.H.1
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(k) In Ref. 1f
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(k) Paterson, I. In Ref. 1f, pp 301-319.
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Paterson, I.1
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(m) Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann E., Eds.; Georg Thieme Verlag: Stuttgart 1713-1735
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(m) Braun, M. In Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp 1603-1666, 1713-1735.
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0343377598
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(b) In Ref. 2a
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(b) Tatsuta, K. In Ref. 2a, pp 1-38.
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Tatsuta, K.1
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0342942239
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(d) In Ref. 2a
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(d) Isobe, M. In Ref. 2a, pp 103-134.
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Isobe, M.1
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0343813212
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(e) In Ref. 2a
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(e) Beau, J.-M. In Ref. 2a, pp 135-182.
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Beau, J.-M.1
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Marco J.A., Carda M., González F., Rodríguez S., Castillo E., Murga J. J. Org. Chem. 63:1998;698-707.
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Murga, J.6
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(d) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961-1963.
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(h) Boons, G.-J.; Downham, R.; Kim, K. S.; Ley, S. V.; Woods, M. Tetrahedron 1994, 50, 7157-7176.
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(j) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
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32
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0003073724
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-
For a Mukaiyama-type aldol reaction on a ketone structurally related to 1, see
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For a Mukaiyama-type aldol reaction on a ketone structurally related to 1, see: Loh, T.-P.; Chua, G.-L.; Vittal, J.-J.; Wong, M.-W. Chem. Commun. 1998, 861-862.
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Loh, T.-P.1
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Wong, M.-W.4
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33
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0027533936
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For a conceptually related synthon based on a dihydroxyacetone derivative, see
-
For a conceptually related synthon based on a dihydroxyacetone derivative, see: Enders, D.; Jegelka, U. Tetrahedron Lett. 1993, 2453-2456. For a recent review on chiral homoenolate equivalents, see: Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365-390.
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Tetrahedron Lett.
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Enders, D.1
Jegelka, U.2
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34
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0033020763
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For a recent review on chiral homoenolate equivalents, see
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For a conceptually related synthon based on a dihydroxyacetone derivative, see: Enders, D.; Jegelka, U. Tetrahedron Lett. 1993, 2453-2456. For a recent review on chiral homoenolate equivalents, see: Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365-390.
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Synthesis
, pp. 365-390
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Ahlbrecht, H.1
Beyer, U.2
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36
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33748899259
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For the preparation of variously protected D- and L-erythrulose derivatives using chiral precursors other than erythrulose itself, see
-
For the preparation of variously protected D- and L-erythrulose derivatives using chiral precursors other than erythrulose itself, see: Marco, J. A.; Carda, M.; González, F.; Rodríguez, S.; Murga, J. Liebigs Ann. Chem. 1996, 1801-1810. For an improved preparation of silylated L-erythrulose acetonides 6 (R=TES, TBS, TPS) from L-erythrulose hydrate, see: Carda, M.; Rodríguez, S.; Murga, J.; Falomir, E.; Marco, J. A.; Röper, H. Synth. Commun. 1999, 29, 2601-2610.
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Marco, J.A.1
Carda, M.2
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Rodríguez, S.4
Murga, J.5
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37
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0032993311
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For an improved preparation of silylated L-erythrulose acetonides 6 (R=TES, TBS, TPS) from L-erythrulose hydrate, see
-
For the preparation of variously protected D- and L-erythrulose derivatives using chiral precursors other than erythrulose itself, see: Marco, J. A.; Carda, M.; González, F.; Rodríguez, S.; Murga, J. Liebigs Ann. Chem. 1996, 1801-1810. For an improved preparation of silylated L-erythrulose acetonides 6 (R=TES, TBS, TPS) from L-erythrulose hydrate, see: Carda, M.; Rodríguez, S.; Murga, J.; Falomir, E.; Marco, J. A.; Röper, H. Synth. Commun. 1999, 29, 2601-2610.
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Carda, M.1
Rodríguez, S.2
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Marco, J.A.5
Röper, H.6
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39
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0025364262
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2NEt
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2NEt: Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
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40
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0030932639
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2NEt
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2NEt: Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653-1661.
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41
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0031930023
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(d) LDA or LDA/LiCl and references cited therein
-
(d) LDA or LDA/LiCl: Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 180-182, and references cited therein.
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Palomo, C.1
González, A.2
García, J.M.3
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Oiarbide, M.5
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Linden, A.7
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44
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33751386593
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Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 58, 147-153. For a general review on boron aldol additions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
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J. Org. Chem.
, vol.58
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Brown, H.C.1
Ganesan, K.2
Dhar, R.K.3
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45
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0001790298
-
-
For a general review on boron aldol additions, see
-
Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 58, 147-153. For a general review on boron aldol additions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
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Org. React.
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Cowden, C.J.1
Paterson, I.2
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46
-
-
0033613760
-
-
A preliminary account of the part of the work described here has already appeared
-
A preliminary account of the part of the work described here has already appeared: Marco, J. A.; Carda, M.; Falomir, E.; Palomo, C.; Oiarbide, M.; Ortiz, J. A.; Linden, A. Tetrahedron Lett. 1999, 1065-1068. For the influence of the protecting groups on the stereoselectivity, see: Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 6845-6848.
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(1999)
Tetrahedron Lett.
, pp. 1065-1068
-
-
Marco, J.A.1
Carda, M.2
Falomir, E.3
Palomo, C.4
Oiarbide, M.5
Ortiz, J.A.6
Linden, A.7
-
47
-
-
0033543725
-
-
For the influence of the protecting groups on the stereoselectivity, see
-
A preliminary account of the part of the work described here has already appeared: Marco, J. A.; Carda, M.; Falomir, E.; Palomo, C.; Oiarbide, M.; Ortiz, J. A.; Linden, A. Tetrahedron Lett. 1999, 1065-1068. For the influence of the protecting groups on the stereoselectivity, see: Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 6845-6848.
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(1999)
Tetrahedron Lett.
, pp. 6845-6848
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-
Carda, M.1
Falomir, E.2
Murga, J.3
Castillo, E.4
González, F.5
Marco, J.A.6
-
48
-
-
0342507914
-
-
The complete details of all reaction conditions, chemical correlations, X-ray diffraction analysis, computational calculations and physical and spectral data of all intermediates are described in the PhD Thesis of E. Falomir (University of Castellón, 1998)
-
The complete details of all reaction conditions, chemical correlations, X-ray diffraction analysis, computational calculations and physical and spectral data of all intermediates are described in the PhD Thesis of E. Falomir (University of Castellón, 1998).
-
-
-
-
49
-
-
0342942233
-
-
Even though any one of the three silyl groups (TES, TBS and TBDPS) is suitable as a protecting group under the reaction conditions of the sequence 7→8→9→10; here we describe only those esters 8 and 9 bearing a TBS group
-
Even though any one of the three silyl groups (TES, TBS and TBDPS) is suitable as a protecting group under the reaction conditions of the sequence 7→8→9→10; here we describe only those esters 8 and 9 bearing a TBS group.
-
-
-
-
51
-
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0030036748
-
-
(b)
-
(b) Xie, M.; Berges, D. A.; Robins, M. J. J. Org. Chem. 1996, 61, 5178-5179.
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Xie, M.1
Berges, D.A.2
Robins, M.J.3
-
52
-
-
0343377587
-
-
The formation of small amounts of the deformylated ester 9 during the oxidative cleavage of 8 could not be avoided: shorter reaction times only led to incomplete oxidation of 7. However, the mixture of 8 and 9 may be used without separation in either of the subsequent reactions, thus improving the overall yields
-
The formation of small amounts of the deformylated ester 9 during the oxidative cleavage of 8 could not be avoided: shorter reaction times only led to incomplete oxidation of 7. However, the mixture of 8 and 9 may be used without separation in either of the subsequent reactions, thus improving the overall yields.
-
-
-
-
53
-
-
0343377586
-
-
The formylated derivatives 8 are quite sensitive to alkaline media. Hydrolysis of 8 under even such mild conditions as potassium carbonate in MeOH at 0°C caused decomposition. The same result was observed when 8 (or 9) was treated with tetra-n-butylammonium fluoride in THF
-
The formylated derivatives 8 are quite sensitive to alkaline media. Hydrolysis of 8 under even such mild conditions as potassium carbonate in MeOH at 0°C caused decomposition. The same result was observed when 8 (or 9) was treated with tetra-n-butylammonium fluoride in THF.
-
-
-
-
54
-
-
0028058771
-
-
Dihydroxy ester 10 (R′=Ph) showed NMR data identical with those reported
-
Dihydroxy ester 10 (R′=Ph) showed NMR data identical with those reported: Wang, Z.-M.; Kolb, H. C.; Sharpless, K. B. J. Org. Chem. 1994, 59, 5104-5105.
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(1994)
J. Org. Chem.
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Wang, Z.-M.1
Kolb, H.C.2
Sharpless, K.B.3
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55
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0028296561
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(a) Palomo, C.; Aizpurua, J. M.; Cabré, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 2725-2728.
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Palomo, C.1
Aizpurua, J.M.2
Cabré, F.3
Cuevas, C.4
Munt, S.5
Odriozola, J.M.6
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57
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(c) Cativiela, C.; Díaz de Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymmetry 1996, 7, 529-536.
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Cativiela, C.1
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0032191772
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(d) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322.
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Merino, P.1
Castillo, E.2
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Merchán, F.L.4
Tejero, T.5
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59
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0033534457
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(e)
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(e) Brackenridge, I., Davies, S. G.; Fenwick, D. R.; Ichihara, O.; Polywka, M. E. C. Tetrahedron 1999, 55, 533-540.
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Brackenridge, I.1
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Polywka, M.E.C.5
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62
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0000265844
-
-
2BCl/tertiary amine to yield E boron enolates, see Ref. 10 and: (a)
-
2BCl/tertiary amine to yield E boron enolates, see Ref. 10 and: (a) Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441-3442.
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63
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(b)
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(b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716-2721.
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Brown, H.C.1
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64
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0001103515
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(c)
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(c) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1992, 57, 3767-3772.
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Brown, H.C.1
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68
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0001346069
-
-
For recent theoretical studies on boron aldol reactions, see: (a)
-
For recent theoretical studies on boron aldol reactions, see: (a) Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493.
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Li, Y.1
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(b)
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(b) Bernardi, A.; Capelli, A. M.; Comotti, A.; Gennari, C.; Gardner, M.; Goodman, J. M.; Paterson, I. Tetrahedron 1991, 47, 3471-3484.
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Bernardi, A.1
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(c) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
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(d) Vulpetti, A.; Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron 1993, 49, 685-696.
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72
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0343377584
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-
Computational ab initio calculations have been performed by Dr J. Murga. The results will be disclosed in due time
-
Computational ab initio calculations have been performed by Dr J. Murga. The results will be disclosed in due time.
-
-
-
-
73
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0342942228
-
-
19 it has been suggested that initial formation of a five-membered chelate involving the boron and the two oxygen atoms, followed by stereoselective deprotonation by the tertiary amine, explain the formation of the putative Z enolate. This and other alternative explanations are now being studied by us at both the theoretical and the experimental level
-
19 it has been suggested that initial formation of a five-membered chelate involving the boron and the two oxygen atoms, followed by stereoselective deprotonation by the tertiary amine, explain the formation of the putative Z enolate. This and other alternative explanations are now being studied by us at both the theoretical and the experimental level.
-
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74
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Paterson I., Norcross R.D., Ward R.A., Romea P., Lister M.A. J. Am. Chem. Soc. 116:1994;11287-11314.
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Lister, M.A.5
|