-
1
-
-
0000999555
-
-
For a seminal reference of Mukaiyama aldol reaction, see
-
For a seminal reference of Mukaiyama aldol reaction, see: Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973, 1011
-
(1973)
Chem. Lett.
, pp. 1011
-
-
Mukaiyama, T.1
Narasaka, K.2
Banno, K.3
-
2
-
-
11844259698
-
-
Mahrwald, R.; Wiley-VCH: Weinheim, Germany, Chapter 2.
-
Ishihara, K.; Yamamoto, H. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, Chapter 2.
-
(2004)
Modern Aldol Reactions
, vol.2
-
-
Ishihara, K.1
Yamamoto, H.2
-
4
-
-
11844259698
-
-
Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, Chapter 7.
-
Denmark, S. E.; Fujimori, S. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, Chapter 7.
-
(2004)
Modern Aldol Reactions
, vol.2
-
-
Denmark, S.E.1
Fujimori, S.2
Mahrwald, R.3
-
5
-
-
33749014701
-
-
McGilvra, J. D.; Unni, A. K.; Modi, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2006, 45, 6130
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 6130
-
-
McGilvra, J.D.1
Unni, A.K.2
Modi, K.3
Rawal, V.H.4
-
6
-
-
58249122146
-
-
Gondi, V. B.; Hagihara, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2009, 48, 776
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 776
-
-
Gondi, V.B.1
Hagihara, K.2
Rawal, V.H.3
-
7
-
-
26444603041
-
-
Zhuang, W.; Poulsen, T. B.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 3284
-
(2005)
Org. Biomol. Chem.
, vol.3
, pp. 3284
-
-
Zhuang, W.1
Poulsen, T.B.2
Jørgensen, K.A.3
-
8
-
-
70349785016
-
-
Asymmetric catalysis of chiral binaphthyl-derived disulfonimides with silyl nucleophiles, see
-
Asymmetric catalysis of chiral binaphthyl-derived disulfonimides with silyl nucleophiles, see: García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 4363
-
-
García-García, P.1
Lay, F.2
García-García, P.3
Rabalakos, C.4
List, B.5
-
9
-
-
78651383697
-
-
Ratjen, L.; García-García, P.; Lay, F.; Beck, M. E.; List, B. Angew. Chem., Int. Ed. 2011, 50, 754
-
(2011)
Angew. Chem., Int. Ed.
, vol.50
, pp. 754
-
-
Ratjen, L.1
García-García, P.2
Lay, F.3
Beck, M.E.4
List, B.5
-
10
-
-
84865428726
-
-
Guin, J.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2012, 51, 8859
-
(2012)
Angew. Chem., Int. Ed.
, vol.51
, pp. 8859
-
-
Guin, J.1
Rabalakos, C.2
List, B.3
-
11
-
-
84870928356
-
-
Mahlau, M.; García-García, P.; List, B. Chem.-Eur. J. 2012, 18, 16283
-
(2012)
Chem. - Eur. J.
, vol.18
, pp. 16283
-
-
Mahlau, M.1
García-García, P.2
List, B.3
-
12
-
-
84874243120
-
-
Gandhi, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 2573
-
(2013)
Angew. Chem., Int. Ed.
, vol.52
, pp. 2573
-
-
Gandhi, S.1
List, B.2
-
13
-
-
84886875117
-
-
Wang, Q.; Leutzsch, M.; van Gemmeren, M.; List, B. J. Am. Chem. Soc. 2013, 135, 15334
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 15334
-
-
Wang, Q.1
Leutzsch, M.2
Van Gemmeren, M.3
List, B.4
-
14
-
-
84905748802
-
-
Ratjen, L.; van Gemmeren, M.; Pesciaioli, F.; List, B. Angew. Chem., Int. Ed. 2014, 53, 8765
-
(2014)
Angew. Chem., Int. Ed.
, vol.53
, pp. 8765
-
-
Ratjen, L.1
Van Gemmeren, M.2
Pesciaioli, F.3
List, B.4
-
15
-
-
84915766639
-
-
Wang, Q.; van Gemmeren, M.; List, B. Angew. Chem., Int. Ed. 2014, 53, 13592
-
(2014)
Angew. Chem., Int. Ed.
, vol.53
, pp. 13592
-
-
Wang, Q.1
Van Gemmeren, M.2
List, B.3
-
17
-
-
84920153803
-
-
Guin, J.; Wang, Q.; van Gemmeren, M.; List, B. Angew. Chem., Int. Ed. 2015, 54, 355.
-
(2015)
Angew. Chem., Int. Ed.
, vol.54
, pp. 355
-
-
Guin, J.1
Wang, Q.2
Van Gemmeren, M.3
List, B.4
Chen, L.-Y.5
He, H.6
Chan, W.-H.7
Lee, A.W.M.8
-
18
-
-
80052184100
-
-
Asymmetric catalysis of chiral binaphthyl-derived disulfonimides as Brønsted acids, see
-
Asymmetric catalysis of chiral binaphthyl-derived disulfonimides as Brønsted acids, see: (k) Chen, L.-Y.; He, H.; Chan, W.-H.; Lee, A. W. M. J. Org. Chem. 2011, 76, 7141
-
(2011)
J. Org. Chem.
, vol.76
, pp. 7141
-
-
Chen, L.-Y.1
He, H.2
Chan, W.-H.3
Lee, A.W.M.4
-
19
-
-
84905857890
-
-
Prévost, S.; Dupré, N.; Leutzsch, M.; Wang, Q.; Wakchaure, V.; List, B. Angew. Chem., Int. Ed. 2014, 53, 8770
-
(2014)
Angew. Chem., Int. Ed.
, vol.53
, pp. 8770
-
-
Prévost, S.1
Dupré, N.2
Leutzsch, M.3
Wang, Q.4
Wakchaure, V.5
List, B.6
Van Gemmeren, M.7
Lay, F.8
List, B.9
-
20
-
-
84901044409
-
-
For a review, see
-
For a review, see: (m) van Gemmeren, M.; Lay, F.; List, B. Aldrichimica Acta 2014, 47, 3.
-
(2014)
Aldrichimica Acta
, vol.47
, pp. 3
-
-
Van Gemmeren, M.1
Lay, F.2
List, B.3
-
22
-
-
0037241494
-
-
TMS silyl enol ether of acetophenone is 103 times less reactive than TMS silyl ketene acetal of methyl isobutylate, see
-
TMS silyl enol ether of acetophenone is 103 times less reactive than TMS silyl ketene acetal of methyl isobutylate, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66
-
(2003)
Acc. Chem. Res.
, vol.36
, pp. 66
-
-
Mayr, H.1
Kempf, B.2
Ofial, A.R.3
-
23
-
-
38349189109
-
-
For reviews on chiral phosphoric acid catalysis, see
-
For reviews on chiral phosphoric acid catalysis, see: Akiyama, T. Chem. Rev. 2007, 107, 5744
-
(2007)
Chem. Rev.
, vol.107
, pp. 5744
-
-
Akiyama, T.1
-
25
-
-
77950248809
-
-
Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395
-
(2010)
Top. Curr. Chem.
, vol.291
, pp. 395
-
-
Kampen, D.1
Reisinger, C.M.2
List, B.3
-
27
-
-
81255211335
-
-
Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156
-
(2011)
Acc. Chem. Res.
, vol.44
, pp. 1156
-
-
Yu, J.1
Shi, F.2
Gong, L.-Z.3
-
28
-
-
79960219398
-
-
Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W.; Atodiresei, I. Angew. Chem., Int. Ed. 2011, 50, 6706
-
(2011)
Angew. Chem., Int. Ed.
, vol.50
, pp. 6706
-
-
Rueping, M.1
Nachtsheim, B.J.2
Ieawsuwan, W.3
Atodiresei, I.4
-
29
-
-
84908249055
-
-
Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047
-
(2014)
Chem. Rev.
, vol.114
, pp. 9047
-
-
Parmar, D.1
Sugiono, E.2
Raja, S.3
Rueping, M.4
-
30
-
-
84935862028
-
-
note
-
For 29Si and 31P NMR spectra, see the Supporting Information.
-
-
-
-
31
-
-
84886007342
-
-
Computational study on the p K a values of various chiral Brønsted acids, see
-
Computational study on the p K a values of various chiral Bronsted acids, see: Kaupmees, K.; Tolstoluzhsky, N.; Raja, S.; Rueping, M.; Leito, I. Angew. Chem., Int. Ed. 2013, 52, 11569
-
(2013)
Angew. Chem., Int. Ed.
, vol.52
, pp. 11569
-
-
Kaupmees, K.1
Tolstoluzhsky, N.2
Raja, S.3
Rueping, M.4
Leito, I.5
-
32
-
-
84900852336
-
-
Yang, C.; Xue, X.-S.; Li, X.; Cheng, J.-P. J. Org. Chem. 2014, 79, 4340
-
(2014)
J. Org. Chem.
, vol.79
, pp. 4340
-
-
Yang, C.1
Xue, X.-S.2
Li, X.3
Cheng, J.-P.4
-
33
-
-
84935869689
-
-
note
-
TMS-A1 and TMS- C1 may exist in equilibrium with their isomers (P- N -SiMe3, P-Se/ O -SiMe3, and S- O -SiMe3).
-
-
-
-
34
-
-
35048832273
-
-
In situ generation of silyl Lewis acids by the reaction of chiral phosphoric acids with silyl compounds, see
-
In situ generation of silyl Lewis acids by the reaction of chiral phosphoric acids with silyl compounds, see: Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12084
-
-
Rowland, E.B.1
Rowland, G.B.2
Rivera-Otero, E.3
Antilla, J.C.4
-
36
-
-
84869037922
-
-
Serdyuk, O. V.; Zamfir, A.; Hampel, F.; Tsogoeva, S. B. Adv. Synth. Catal. 2012, 354, 3115
-
(2012)
Adv. Synth. Catal.
, vol.354
, pp. 3115
-
-
Serdyuk, O.V.1
Zamfir, A.2
Hampel, F.3
Tsogoeva, S.B.4
-
37
-
-
84935897870
-
-
note
-
The reason for such a reactivity difference of the catalysts remains unclear, and computational studies to rationalize this result are underway.
-
-
-
-
38
-
-
49849086423
-
-
For the beneficial effect of bulky para substituents at the 3,3′-aryl groups on enantioselectivity in chiral phosphoric acid catalysis, see
-
For the beneficial effect of bulky para substituents at the 3,3′-aryl groups on enantioselectivity in chiral phosphoric acid catalysis, see: Cheng, X.; Goddard, R.; Buth, G.; List, B. Angew. Chem., Int. Ed. 2008, 47, 5079
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 5079
-
-
Cheng, X.1
Goddard, R.2
Buth, G.3
List, B.4
-
39
-
-
56749163583
-
-
Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 15786
-
-
Cheng, X.1
Vellalath, S.2
Goddard, R.3
List, B.4
-
41
-
-
53249085441
-
-
Jiao, P.; Nakashima, D.; Yamamoto, H. Angew. Chem., Int. Ed. 2008, 47, 2411
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 2411
-
-
Jiao, P.1
Nakashima, D.2
Yamamoto, H.3
-
42
-
-
84935881930
-
-
note
-
It is reported that the substituent on the sulfonyl group of the phosphoramide catalyst has a significant influence on the yield but not on the enantioselectivity; see: ref 10f and references therein.
-
-
-
-
43
-
-
0037037846
-
-
For usage of this base to differentiate the reaction pathway between Lewis acid and Bronsted acid catalysis, see
-
For usage of this base to differentiate the reaction pathway between Lewis acid and Bronsted acid catalysis, see: Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219
-
(2002)
Tetrahedron
, vol.58
, pp. 8219
-
-
Mathieu, B.1
Ghosez, L.2
-
44
-
-
29444449562
-
-
Hara, K.; Akiyama, R.; Sawamura, M. Org. Lett. 2005, 7, 5621
-
(2005)
Org. Lett.
, vol.7
, pp. 5621
-
-
Hara, K.1
Akiyama, R.2
Sawamura, M.3
-
45
-
-
84935890343
-
-
note
-
This result implies that our new catalyst has the potential to enable the asymmetric anti -selective Mukaiyama aldol reaction.
-
-
-
-
46
-
-
84935866169
-
-
note
-
Treatment of a 1.5:1 mixture of E-and Z-1b with 5 mol % of catalyst B4 at -100 C for 1 h resulted in a 1:7.7 mixture of E-and Z-1b, see the Supporting Information.
-
-
-
-
47
-
-
0031832945
-
-
For examples of Brønsted acid-catalyzed isomerization of silyl enol ethers, see
-
For examples of Brønsted acid-catalyzed isomerization of silyl enol ethers, see: Deyine, A.; Dujardin, G.; Mammeri, M.; Poirier, J.-M. Synth. Commun. 1998, 28, 1817
-
(1998)
Synth. Commun.
, vol.28
, pp. 1817
-
-
Deyine, A.1
Dujardin, G.2
Mammeri, M.3
Poirier, J.-M.4
-
48
-
-
0001005279
-
-
Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6444
-
-
Ishihara, K.1
Nakamura, H.2
Nakamura, S.3
Yamamoto, H.4
-
49
-
-
84860620491
-
-
Inanaga, K.; Ogawa, Y.; Nagamoto, Y.; Daigaku, A.; Tokuyama, H.; Takemoto, Y.; Takasu, K. Beilstein J. Org. Chem. 2012, 8, 658
-
(2012)
Beilstein J. Org. Chem.
, vol.8
, pp. 658
-
-
Inanaga, K.1
Ogawa, Y.2
Nagamoto, Y.3
Daigaku, A.4
Tokuyama, H.5
Takemoto, Y.6
Takasu, K.7
-
50
-
-
0003913629
-
-
For reviews on catalytic asymmetric allylation of carbonyl compounds with allylsilanes, see: In; Wiley-VCH: Weinheim, Germany, Chapter 10.
-
For reviews on catalytic asymmetric allylation of carbonyl compounds with allylsilanes, see: Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 10.
-
(2000)
Modern Carbonyl Chemistry
-
-
Denmark, S.E.1
Almstead, N.G.2
Otera, J.3
-
52
-
-
50249134990
-
-
Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 1560
-
-
Denmark, S.E.1
Beutner, G.L.2
-
53
-
-
83755178261
-
-
Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774
-
(2011)
Chem. Rev.
, vol.111
, pp. 7774
-
-
Yus, M.1
González-Gómez, J.C.2
Foubelo, F.3
-
54
-
-
84935917535
-
-
note
-
Unsubstituted or γ-substituted allylsilanes did not react even at room temperature.
-
-
-
-
55
-
-
45549084536
-
-
Kawasaki, M.; Li, P.; Yamamoto, H. Angew. Chem., Int. Ed. 2008, 47, 3795
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 3795
-
-
Kawasaki, M.1
Li, P.2
Yamamoto, H.3
|