-
1
-
-
36849024926
-
-
(a) Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133.
-
(2007)
Chem. Rev
, vol.107
, pp. 5133
-
-
Mellah, M.1
Voituriez, A.2
Schulz, E.3
-
2
-
-
38049036296
-
-
(b) Blaser, H.-U.; Pugin, B.; Spindler, F.; Thommen, M. Acc. Chem. Res. 2007, 40, 1240.
-
(2007)
Acc. Chem. Res
, vol.40
, pp. 1240
-
-
Blaser, H.-U.1
Pugin, B.2
Spindler, F.3
Thommen, M.4
-
3
-
-
38049077372
-
-
Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.
-
(2007)
Acc. Chem. Res
, vol.40
, pp. 1278
-
-
Zhang, W.1
Chi, Y.2
Zhang, X.3
-
5
-
-
33749828310
-
-
(e) Desimoni, G.; Faita, G.; Jorgensen, K. A. Chet Th J Rev. 2006, 106, 3561.
-
(2006)
Chet Th J Rev
, vol.106
, pp. 3561
-
-
Desimoni, G.1
Faita, G.2
Jorgensen, K.A.3
-
7
-
-
85026862495
-
-
For a 100 g scale synthesis of (R, R)-1 from benzoin, see: Ikariya, T.; Hashiguchi, S.; Murata, K.; Noyori, R. Org. Synth. 2005, 82, 10.
-
For a 100 g scale synthesis of (R, R)-1 from benzoin, see: Ikariya, T.; Hashiguchi, S.; Murata, K.; Noyori, R. Org. Synth. 2005, 82, 10.
-
-
-
-
8
-
-
0001462791
-
-
For a 1 kg scale synthesis of (R,R)-1 from trans-stilbene, see: Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302.
-
For a 1 kg scale synthesis of (R,R)-1 from trans-stilbene, see: Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302.
-
-
-
-
9
-
-
66149100881
-
-
Current Aldrich prices for (R,R)-1: $2.11(CDN)/mmol. For comparison purposes the price of (R)-BINOL is $16.35(CDN)/mmol.
-
Current Aldrich prices for (R,R)-1: $2.11(CDN)/mmol. For comparison purposes the price of (R)-BINOL is $16.35(CDN)/mmol.
-
-
-
-
10
-
-
33749247211
-
-
For example, see: a
-
For example, see: (a) Broeker, J.; Knollmueller, M.; Gaertner, P. Tetrahedron: Asymmetry 2006, 17, 2413.
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 2413
-
-
Broeker, J.1
Knollmueller, M.2
Gaertner, P.3
-
11
-
-
0034699265
-
-
(b) Andrus, M. B.; Sekhar, B. B. V. S.; Meredith, E. L.; Dalley, N. K. Org. Lett. 2000, 2, 3035.
-
(2000)
Org. Lett
, vol.2
, pp. 3035
-
-
Andrus, M.B.1
Sekhar, B.B.V.S.2
Meredith, E.L.3
Dalley, N.K.4
-
12
-
-
4444327065
-
-
Kim, K. S.; Lee, Y. J.; Kim, J. H.; Sung, D. K. Chem. Commun. 2002, 1116.
-
(2002)
Chem. Commun
, pp. 1116
-
-
Kim, K.S.1
Lee, Y.J.2
Kim, J.H.3
Sung, D.K.4
-
13
-
-
0035859705
-
-
Mazé, F.; Purpura, M.; Bernaud, F.; Mangeney, P.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 1957.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 1957
-
-
Mazé, F.1
Purpura, M.2
Bernaud, F.3
Mangeney, P.4
Alexakis, A.5
-
15
-
-
37049082801
-
-
(f) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293.
-
(1995)
J. Chem. Soc., Perkin Trans. 1
, pp. 2293
-
-
Wallace, T.W.1
Wardell, I.2
Li, K.-D.3
Leeming, P.4
Redhouse, A.D.5
Challand, S.R.6
-
16
-
-
0029123746
-
-
(g) Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 2113
-
-
Fujioka, H.1
Kitagawa, H.2
Nagatomi, Y.3
Kita, Y.4
-
17
-
-
33744791834
-
-
For examples of chiral phosphepines and thiepines that incorporate hydrobenzoin, see: (a) Wyatt, P, Hudson, A, Charmant, J, Orpen, A. G, Phetmung, H. Org. Biomol. Chem. 2006, 4, 2218
-
For examples of chiral phosphepines and thiepines that incorporate hydrobenzoin, see: (a) Wyatt, P.; Hudson, A.; Charmant, J.; Orpen, A. G.; Phetmung, H. Org. Biomol. Chem. 2006, 4, 2218.
-
-
-
-
18
-
-
0035819735
-
-
and references therein
-
(b) Wyatt, P.; Warren, S.; McPartlin, M.; Woodroffe, T. J. Chem. Soc., Perkin Trans. 1 2001, 279, and references therein.
-
(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 279
-
-
Wyatt, P.1
Warren, S.2
McPartlin, M.3
Woodroffe, T.4
-
19
-
-
46049109527
-
-
For example, see: a
-
For example, see: (a) Rauniyar, V.; Zhai, H.; Hall, D. G. J. Am. Chem. Soc. 2008, 130, 8481.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 8481
-
-
Rauniyar, V.1
Zhai, H.2
Hall, D.G.3
-
20
-
-
17044400104
-
-
(b) Mlynarski, J.; Jankowska, J.; Rakiel, B. Tetrahedron: Asymmetry 2005, 16, 1521.
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 1521
-
-
Mlynarski, J.1
Jankowska, J.2
Rakiel, B.3
-
23
-
-
5244362549
-
-
(e) Amurrio, D.; Khan, K.; Kiindig, E. P. J. Org. Chem. 1996, 61, 2258.
-
(1996)
J. Org. Chem
, vol.61
, pp. 2258
-
-
Amurrio, D.1
Khan, K.2
Kiindig, E.P.3
-
24
-
-
12444317008
-
-
(f) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 8266
-
-
Tomioka, K.1
Shindo, M.2
Koga, K.3
-
25
-
-
66149158460
-
-
For the synthesis of ortho-substituted hydrobenzoin derivatives, see refs 5f, 6a, 6b, 7a, and 7d
-
For the synthesis of ortho-substituted hydrobenzoin derivatives, see refs 5f, 6a, 6b, 7a, and 7d.
-
-
-
-
26
-
-
66149090695
-
-
The synthesis of ortho-functionalized hydrobenzoins typically involves McMurry coupling of an ortho-substituted benzaldehdye, followed by I2-catalyzed isomerization of the resulting stilbene and Sharpless asymmetric dihydroxylation. For examples where Sharpless asymmetric dihydroxylation of ortho-functionalized trans-stilbenes fails to provide the desired diol, see ref 7a
-
2-catalyzed isomerization of the resulting stilbene and Sharpless asymmetric dihydroxylation. For examples where Sharpless asymmetric dihydroxylation of ortho-functionalized trans-stilbenes fails to provide the desired diol, see ref 7a.
-
-
-
-
27
-
-
66149143092
-
-
For complications associated with the optical enrichment of hydrobenzoin derivatives by crystallization, see ref 7d
-
For complications associated with the optical enrichment of hydrobenzoin derivatives by crystallization, see ref 7d.
-
-
-
-
28
-
-
33749522044
-
-
Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 13070
-
-
Akiyama, T.1
Morita, H.2
Fuchibe, K.3
-
30
-
-
66149139761
-
-
For examples of ortho-metalation reactions involving a benzyl alcohol or a-methylbenzyl alcohol, see
-
For examples of ortho-metalation reactions involving a benzyl alcohol or a-methylbenzyl alcohol, see:
-
-
-
-
31
-
-
0037458695
-
-
(a) Granander, J.; Sott, R.; Hilmersson, G. Tetrahedron: Asymmetry 2003, 14, 439.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 439
-
-
Granander, J.1
Sott, R.2
Hilmersson, G.3
-
32
-
-
0001082990
-
-
(b) Hirt, U. H.; Spingler, B.; Wirth, T. J. Org. Chem. 1998, 63, 7674.
-
(1998)
J. Org. Chem
, vol.63
, pp. 7674
-
-
Hirt, U.H.1
Spingler, B.2
Wirth, T.3
-
33
-
-
0000483399
-
-
Panetta, C. A.; Garlick, S. M.; Durst, H. D.; Longo, F. R.; Ward, J. R. J. Org. Chem. 1990, 55, 5202.
-
(1990)
J. Org. Chem
, vol.55
, pp. 5202
-
-
Panetta, C.A.1
Garlick, S.M.2
Durst, H.D.3
Longo, F.R.4
Ward, J.R.5
-
34
-
-
84985520791
-
-
Meyer, N.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1978, 17, 521.
-
(1978)
Angew. Chem., Int. Ed. Engl
, vol.17
, pp. 521
-
-
Meyer, N.1
Seebach, D.2
-
35
-
-
66149092235
-
-
For a conceptually related but less direct approach to functionalized hydrobenzoins, see refs 6a and 6b
-
For a conceptually related but less direct approach to functionalized hydrobenzoins, see refs 6a and 6b.
-
-
-
-
36
-
-
0033570258
-
-
While it is unlikely that any epimerization of (R,R)-hydrobenzoin could occur during this process, the optical purity of (R,R)-hydrobenzoin recovered from the treatment of the tetraanion 10 with H2O was confirmed by chiral GC analysis. In addition, the 1H NMR spectra of the crude product contained none of the corresponding meso-hydrobenzoin, which can be differentiated from dl-hydrobenzoin by the chemical shift of the benzyl protons. 1H NMR (CDCl3) δ: 4.72 ppm (dl-hydrobenzoin, 4.80 ppm meso- hydrobenzoin, Periasamy, M, Srinivas, G, Karunakar, G. V, Bharathi, P. Tetrahedron Lett. 1999, 40, 7577
-
3) δ: 4.72 ppm (dl-hydrobenzoin); 4.80 ppm (meso- hydrobenzoin). Periasamy, M.; Srinivas, G.; Karunakar, G. V.; Bharathi, P. Tetrahedron Lett. 1999, 40, 7577.
-
-
-
-
37
-
-
33847612747
-
-
For mechanistic analyses of DoM reactions, see: a
-
For mechanistic analyses of DoM reactions, see: (a) Chadwick, S. T.; Ramirez, A.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2007, 129. 2259.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 2259
-
-
Chadwick, S.T.1
Ramirez, A.2
Gupta, L.3
Collum, D.B.4
-
39
-
-
3242659209
-
-
Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 2206
-
-
Whisler, M.C.1
MacNeil, S.2
Snieckus, V.3
Beak, P.4
-
40
-
-
0141794090
-
-
Slocum, D. W.; Dumbris, S.; Brown, S.; Jackson, G.; LaMastus, R.; Mullins, E.; Ray, J.; Shelton, P.; Walstrom, A.; Wilcox, J. M.; Holman, R. W. Tetrahedron 2003, 59, 8275.
-
(2003)
Tetrahedron
, vol.59
, pp. 8275
-
-
Slocum, D.W.1
Dumbris, S.2
Brown, S.3
Jackson, G.4
LaMastus, R.5
Mullins, E.6
Ray, J.7
Shelton, P.8
Walstrom, A.9
Wilcox, J.M.10
Holman, R.W.11
-
41
-
-
0034644389
-
-
(e) Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 8640
-
-
Chadwick, S.T.1
Rennels, R.A.2
Rutherford, J.L.3
Collum, D.B.4
-
42
-
-
66149094616
-
-
Repetition of this reaction with 4 or 5 equiv of n-BuLi (reflux, 16 h) provided 14 in 19% or 34% isolated yield, respectively.
-
Repetition of this reaction with 4 or 5 equiv of n-BuLi (reflux, 16 h) provided 14 in 19% or 34% isolated yield, respectively.
-
-
-
-
43
-
-
66149122189
-
-
Examples of electrophiles that proved incompatible with 10 and/ or provided the desired product in very low yield (<10%) include benzaldehyde, acetone, acetaldehyde, diethylcarbonate, valeraldehyde, tri- methylsilyl chloride, cyclohexanal, crotonaldehyde, paraformaldehyde, formaldehyde, dimethylformamide, and benzylbromide.
-
Examples of electrophiles that proved incompatible with 10 and/ or provided the desired product in very low yield (<10%) include benzaldehyde, acetone, acetaldehyde, diethylcarbonate, valeraldehyde, tri- methylsilyl chloride, cyclohexanal, crotonaldehyde, paraformaldehyde, formaldehyde, dimethylformamide, and benzylbromide.
-
-
-
-
44
-
-
66149085210
-
-
The acetonide 19 was prepared in >97% yield by treating a solution of 14 in dimethoxypropane with a catalytic amount of HCl.
-
The acetonide 19 was prepared in >97% yield by treating a solution of 14 in dimethoxypropane with a catalytic amount of HCl.
-
-
-
-
45
-
-
0035982921
-
-
Attempts to directly couple the diol 14 with aryl boronic acids resulted primarily in the formation of cM-4b,9b-dihydrobenzofuro[3,2- ftjbenzofuran. For an unrelated synthesis of this substance, see: Masutani, K.; Irie, R.; Katsuki, T. Chem. Lett. 2002,36.
-
Attempts to directly couple the diol 14 with aryl boronic acids resulted primarily in the formation of cM-4b,9b-dihydrobenzofuro[3,2- ftjbenzofuran. For an unrelated synthesis of this substance, see: Masutani, K.; Irie, R.; Katsuki, T. Chem. Lett. 2002,36.
-
-
-
-
46
-
-
29844433863
-
-
Attempts to effect the cross-coupling of 19 with pyridine W-oxide following the procedure reported in Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020 led predominantly to the formation of the acetonide of dihydro-phenanthrenediol.
-
Attempts to effect the cross-coupling of 19 with pyridine W-oxide following the procedure reported in Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020 led predominantly to the formation of the acetonide of dihydro-phenanthrenediol.
-
-
-
-
47
-
-
0001048218
-
-
-1 for the B-O stretching modes in 3-methyl-2,1-benzoxaborol, we have tentatively assigned the structure for 17 as shown in Scheme 2. See: Dale, W. J.; Rush, J. E. J. Org. Chem. 1962, 27, 2598.
-
-1 for the B-O stretching modes in 3-methyl-2,1-benzoxaborol, we have tentatively assigned the structure for 17 as shown in Scheme 2. See: Dale, W. J.; Rush, J. E. J. Org. Chem. 1962, 27, 2598.
-
-
-
-
48
-
-
0025816845
-
-
Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Snieckus, V.; Josephy, P. D. J. Org. Chem. 1991, 56, 3763.
-
(1991)
J. Org. Chem
, vol.56
, pp. 3763
-
-
Alo, B.I.1
Kandil, A.2
Patil, P.A.3
Sharp, M.J.4
Siddiqui, M.A.5
Snieckus, V.6
Josephy, P.D.7
-
49
-
-
66149086882
-
-
3, EtOH, DME, reflux) provided the cyclooctenyl precursor to 6 in 17% isolated yield.
-
3, EtOH, DME, reflux) provided the cyclooctenyl precursor to 6 in 17% isolated yield.
-
-
-
-
50
-
-
0035951550
-
-
Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633.
-
(2001)
J. Org. Chem
, vol.66
, pp. 633
-
-
Simon, J.1
Salzbrunn, S.2
Prakash, G.K.S.3
Petasis, N.A.4
Olah, G.A.5
-
51
-
-
0030058386
-
-
The acetonide of 24 has been synthesized in 6% overall yield following a six-step sequence of reactions. See: Yamamoto, H.; Kobayashi, S.; Kanemasa, S. Tetrahedron Asymmetry 1996, 7, 149.
-
The acetonide of 24 has been synthesized in 6% overall yield following a six-step sequence of reactions. See: Yamamoto, H.; Kobayashi, S.; Kanemasa, S. Tetrahedron Asymmetry 1996, 7, 149.
-
-
-
|