-
1
-
-
0035136250
-
-
(a) Ariza, X.; Garcia, J.; López, M.; Montserrat, L. Synlett 2001, 120-122.
-
(2001)
Synlett
, pp. 120-122
-
-
Ariza, X.1
Garcia, J.2
López, M.3
Montserrat, L.4
-
2
-
-
0346057822
-
-
(b) Ariza, X.; Fernández, N.; Garcia, J.; López, M.; Montserrat, L.; Ortiz, J. Synthesis 2004, 128-134.
-
(2004)
Synthesis
, pp. 128-134
-
-
Ariza, X.1
Fernández, N.2
Garcia, J.3
López, M.4
Montserrat, L.5
Ortiz, J.6
-
3
-
-
3542996614
-
-
note
-
4 reduction and partial hydrogenation, respectively (see ref 1).
-
-
-
-
4
-
-
0026531007
-
-
See, for example: (a) Grabley, S.; Granzer, E.; Huetter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.; Till, G.; Phillipps, S.; Wink, J.; Zeeck, A. J. Antibiot. 1992, 45, 56-65.
-
(1992)
J. Antibiot.
, vol.45
, pp. 56-65
-
-
Grabley, S.1
Granzer, E.2
Huetter, K.3
Ludwig, D.4
Mayer, M.5
Thiericke, R.6
Till, G.7
Phillipps, S.8
Wink, J.9
Zeeck, A.10
-
6
-
-
0034716726
-
-
(c) Arnone, A.; Nasini, G.; de Pava, O. V. Phytochemistry 2000, 53, 1087-1090.
-
(2000)
Phytochemistry
, vol.53
, pp. 1087-1090
-
-
Arnone, A.1
Nasini, G.2
De Pava, O.V.3
-
8
-
-
0000458209
-
-
For a review on substrate-directable chemical reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
-
(1993)
Chem. Rev.
, vol.93
, pp. 1307-1370
-
-
Hoveyda, A.H.1
Evans, D.A.2
Fu, G.C.3
-
9
-
-
0027245910
-
-
Current preparations of enantiopure saturated 1,4-diols include: Enzymatic resolutions of mixtures of meso and racemic isomers: (a) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1993, 4, 925-930.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 925-930
-
-
Mattson, A.1
Öhrner, N.2
Hult, K.3
Norin, T.4
-
13
-
-
0033001550
-
-
and references therein
-
Dynamic kinetic resolution: (e) Persson, B. A.; Huerta, F. F.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 5237-5240 and references therein.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5237-5240
-
-
Persson, B.A.1
Huerta, F.F.2
Bäckvall, J.-E.3
-
15
-
-
0025886768
-
-
(g) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569-592.
-
(1991)
Tetrahedron: Asymmetry
, vol.2
, pp. 569-592
-
-
Burk, M.J.1
Feaster, J.E.2
Harlow, R.L.3
-
16
-
-
0000956274
-
-
Microbial reduction of diketones using baker's yeast: (h) Lieser, J. K. Synth. Commun. 1983, 13, 765-767.
-
(1983)
Synth. Commun.
, vol.13
, pp. 765-767
-
-
Lieser, J.K.1
-
19
-
-
0342995737
-
-
For a review on the synthesis of 2,5-disubstituted pyrrolidines, see: (a) Pichon, M.; Figadère, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 927-964
-
-
Pichon, M.1
Figadère, B.2
-
21
-
-
0028926606
-
-
See also ref 5b
-
(c) Chong, J. M.; Clarke, I. S.; Koch, I.; Olbach, P. C.; Taylor, N. J. Tetrahedron: Asymmetry 1995, 6, 409-418. See also ref 5b.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 409-418
-
-
Chong, J.M.1
Clarke, I.S.2
Koch, I.3
Olbach, P.C.4
Taylor, N.J.5
-
22
-
-
0344382102
-
-
(a) Otten, S.; Frölich, R.; Haufe, G. Tetrahedron: Asymmetry 1998, 9, 189-191.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 189-191
-
-
Otten, S.1
Frölich, R.2
Haufe, G.3
-
23
-
-
0000421034
-
-
(b) Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J. Org. Chem. 1998, 63, 4532-4534.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4532-4534
-
-
Julienne, K.1
Metzner, P.2
Henryon, V.3
Greiner, A.4
-
26
-
-
0000585749
-
-
and references therein See also ref 5g
-
(c) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424 and references therein. See also ref 5g.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 4423-4424
-
-
Burk, M.J.1
Harper, T.G.P.2
Kalberg, C.S.3
-
27
-
-
0037041356
-
-
(a) Amador, M.; Ariza, X.; Garcia, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 2691-2694
-
-
Amador, M.1
Ariza, X.2
Garcia, J.3
Ortiz, J.4
-
28
-
-
0037037959
-
-
See also: (b) Diez, R. S.; Adger, B.; Carreira, E. M. Tetrahedron 2002, 58, 8341-8344.
-
(2002)
Tetrahedron
, vol.58
, pp. 8341-8344
-
-
Diez, R.S.1
Adger, B.2
Carreira, E.M.3
-
29
-
-
3543040999
-
-
note
-
In many cases, the aldehyde is partially consumed in the formation of self-condensation aldol products.
-
-
-
-
30
-
-
0000846718
-
-
(a) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Vilarrasa, J. Org. Chem. 1996, 61, 9021-9025.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9021-9025
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
Loscertales, T.4
Vilarrasa5
-
31
-
-
0028802842
-
-
For related reductions, see: (b) Corey, E. J., Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 9153-9156
-
-
Corey, E.J.1
Helal, C.J.2
-
33
-
-
0032480917
-
-
In this connection, it should be noted that the oxazaborolidine-mediated reduction of the related (E)-alk-2-ene-1,4-diones affords 1,4-diols 2 in good yields and enantioselectivities but, in general, suffers from low diastereoselectivities (dl/meso ratio from 5.6:1 to ∼1:1). In contrast, (Z)-alk-2-ene-1,4-diones give low yields of the desired (Z)-1,4-diol 3 under the same conditions. See: Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947-14962.
-
(1998)
Tetrahedron
, vol.54
, pp. 14947-14962
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
López, M.4
Manzanal, J.5
Vilarrasa, J.6
-
34
-
-
0002736658
-
-
For a discussion of this statistical effect applied to two-directional chain syntheses, see: Poss C. S.; Schreiber S. L. Acc. Chem. Res. 1994, 27, 9-17.
-
(1994)
Acc. Chem. Res.
, vol.27
, pp. 9-17
-
-
Poss, C.S.1
Schreiber, S.L.2
-
36
-
-
0031562081
-
-
A part of this work appeared as a preliminary communication: Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091-1094.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 1091-1094
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
Loscertales, T.4
Manzanal, J.5
Vilarrasa, J.6
-
38
-
-
33646850080
-
-
Sudweeks, W. B.; Broadbent, H. S. J. Org. Chem. 1975, 40, 1131-1136. These authors described the preparation of 1d and 1e in 32% and 31% using the magnesium acetylide. We obtained better results (76% and 98% yield, respectively) by using the dilithium acetylide. However, when α-unbranched aldehydes as propanal were used, much lower yields were recorded.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 1131-1136
-
-
Sudweeks, W.B.1
Broadbent, H.S.2
-
39
-
-
3543034374
-
-
note
-
Reduction of diketone 5f using 0.2 mmol of catalyst led to a complex mixture from which diol (R,R)-1f was isolated in low yield. This disappointing result was not completely unexpected in the light of our previous experience in the reduction of the related 1,4-diphenylbut-2-ene-1,4-dione (see ref 12).
-
-
-
-
40
-
-
3543031960
-
-
note
-
2, Pt/C) of 1 with that given in the literature (see refs 12 and 14 and references therein).
-
-
-
-
41
-
-
0032541271
-
-
For a review, see: Corey, E. J.; Helal, Angew. Chem., Int. Ed. Engl. 1998, 37, 1986-2012.
-
(1998)
Angew. Chem., Int. Ed. Engl.
, vol.37
, pp. 1986-2012
-
-
Corey, E.J.1
Helal2
-
42
-
-
0034680698
-
-
Alemany, C.; Bach, J.; Garcia, J.; López, M.; Rodriguez, A. B. Tetrahedron 2000, 56, 9305-9312.
-
(2000)
Tetrahedron
, vol.56
, pp. 9305-9312
-
-
Alemany, C.1
Bach, J.2
Garcia, J.3
López, M.4
Rodriguez, A.B.5
-
44
-
-
0001542996
-
-
(b) Quallich, G. J.; Blake, J. F.; Woodall, T. M. J. Am. Chem. Soc. 1994, 116, 8516-8525.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 8516-8525
-
-
Quallich, G.J.1
Blake, J.F.2
Woodall, T.M.3
-
45
-
-
3543008052
-
-
Transformation of 1a into 9a by treatment with bromine in chloroform was described almost a century ago: (a) Dupont, M. G. C. R. Acad. Sci. 1909, 149, 1381-1383.
-
(1909)
C. R. Acad. Sci.
, vol.149
, pp. 1381-1383
-
-
Dupont, M.G.1
-
47
-
-
37049078388
-
-
(c) Schoepfer, J.; Eichenberger, E.; Neier, R. J. Chem. Soc., Chem. Commun. 1993,246-248.
-
(1993)
J. Chem. Soc., Chem. Commun.
, pp. 246-248
-
-
Schoepfer, J.1
Eichenberger, E.2
Neier, R.3
-
48
-
-
0027205478
-
-
The use of bromine in the presence of Hünig's base has been also reported: (d) Adjé, N.; Breuilles, P.; Uguen, D. Tetrahedron Lett. 1993, 34, 4631-4634.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 4631-4634
-
-
Adjé, N.1
Breuilles, P.2
Uguen, D.3
-
49
-
-
3543014134
-
-
note
-
i symmetry). In contrast, the dipole moment for the minimum energy conformations of dl-2a and dl-9a are 0.01 and 2.46 D, respectively.
-
-
-
-
50
-
-
0030599660
-
-
Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1998, 37, 9313-9316.
-
(1998)
Tetrahedron Lett.
, vol.37
, pp. 9313-9316
-
-
Yanada, R.1
Negoro, N.2
Yanada, K.3
Fujita, T.4
-
51
-
-
0032510179
-
-
Malanga, C.; Mannucci, S.; Lardicci, L. Tetrahedron 1998, 54, 1021-1028.
-
(1998)
Tetrahedron
, vol.54
, pp. 1021-1028
-
-
Malanga, C.1
Mannucci, S.2
Lardicci, L.3
-
53
-
-
0000469912
-
-
Butcher, T. S.; Zhou, F.; Detty, M. R. J. Org. Chem. 1998, 63, 169-176.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 169-176
-
-
Butcher, T.S.1
Zhou, F.2
Detty, M.R.3
-
56
-
-
33947290986
-
-
(b) Lalezari, I.; Shafiee, A.; Yalpani, M. J. Org. Chem. 1971, 36, 2836-2838.
-
(1971)
J. Org. Chem.
, vol.36
, pp. 2836-2838
-
-
Lalezari, I.1
Shafiee, A.2
Yalpani, M.3
-
58
-
-
3542996613
-
-
note
-
4 reduction of diketone 5g gave a ∼1:1 mixture of dl-1g and meso-1g.
-
-
-
-
59
-
-
37049098631
-
-
(a) Acheson, R. M.; Bite, M. G.; Cooper, M. W. J. Chem. Soc., Perkin Trans. 1 1976, 1908-1911.
-
(1976)
J. Chem. Soc., Perkin Trans. 1
, pp. 1908-1911
-
-
Acheson, R.M.1
Bite, M.G.2
Cooper, M.W.3
-
61
-
-
0010640653
-
-
Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
-
(1969)
J. Org. Chem.
, vol.34
, pp. 2543-2549
-
-
Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
-
62
-
-
33751385008
-
-
Kim, M.-J.; Lee, I. S.; Jeong, N.; Choi, Y. K. J. Org. Chem. 1993, 58, 6483-6485.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 6483-6485
-
-
Kim, M.-J.1
Lee, I.S.2
Jeong, N.3
Choi, Y.K.4
-
63
-
-
0020833984
-
-
Saimoto, H.; Shinoda, M.; Matsubara, S.; Oshima, K.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 3088-3092.
-
(1983)
Bull. Chem. Soc. Jpn.
, vol.56
, pp. 3088-3092
-
-
Saimoto, H.1
Shinoda, M.2
Matsubara, S.3
Oshima, K.4
Hiyama, T.5
Nozaki, H.6
|