-
2
-
-
77955699909
-
-
WO 2005086661
-
Akerman, M.; Houze, J.; Lin, D. C. H.; Liu, J.; Luo, J.; Medina, J. C.; Qiu, W.; Reagan, J. D.; Sharma, R.; Shuttleworth, S. J.; Sun, Y.; Zhang, J.; Zhu, L. Int. Appl. PCT, WO 2005086661, 2005.
-
(2005)
Int. Appl. PCT
-
-
Akerman, M.1
Houze, J.2
Lin, D.C.H.3
Liu, J.4
Luo, J.5
Medina, J.C.6
Qiu, W.7
Reagan, J.D.8
Sharma, R.9
Shuttleworth, S.J.10
Sun, Y.11
Zhang, J.12
Zhu, L.13
-
3
-
-
77955705584
-
-
in preparation
-
Walker, S. D., Borths, C.; DiVirgilio, E.; Faul, M. M.; Huang, L.; Liu, P.; Woo, J. C. S., in preparation.
-
-
-
Walker, S.D.1
Borths, C.2
Divirgilio, E.3
Faul, M.M.4
Huang, L.5
Liu, P.6
Woo, J.C.S.7
-
4
-
-
74949097468
-
-
Part of this work has been communicated: S. Cui, S.D. Walker, J.C.S. Woo, C.J. Borths, H. Mukherjee, M.J. Chen, and M.M. Faul J. Am. Chem. Soc. 132 2010 436
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 436
-
-
Cui, S.1
Walker, S.D.2
Woo, J.C.S.3
Borths, C.J.4
Mukherjee, H.5
Chen, M.J.6
Faul, M.M.7
-
10
-
-
33845281609
-
-
L.F. Tietze, S. Brand, T. Pfeiffer, J. Antel, K. Harms, and G.M. Sheldrick J. Am. Chem. Soc. 109 1987 921
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 921
-
-
Tietze, L.F.1
Brand, S.2
Pfeiffer, T.3
Antel, J.4
Harms, K.5
Sheldrick, G.M.6
-
17
-
-
77955699458
-
-
See Experimental Section.
-
See Experimental Section.
-
-
-
-
23
-
-
77955700111
-
-
For the review of the Meldrum's acids, see:
-
For the review of the Meldrum's acids, see:
-
-
-
-
24
-
-
0344814478
-
-
B.C. Chen Heterocycles 32 1991 529 For recent examples of other conjugate additions using Meldrum's acids derived acceptors as the substrates, see:
-
(1991)
Heterocycles
, vol.32
, pp. 529
-
-
Chen, B.C.1
-
35
-
-
77955700553
-
-
For recent reviews of asymmetric conjugate alkynylation, see:
-
For recent reviews of asymmetric conjugate alkynylation, see:
-
-
-
-
36
-
-
54849427261
-
-
S. Fujimori, T.F. Knöpfel, P. Zarotti, T. Ichikawa, D. Boyall, and E.M. Carreira Bull. Chem. Soc. Jpn. 80 2007 1635
-
(2007)
Bull. Chem. Soc. Jpn.
, vol.80
, pp. 1635
-
-
Fujimori, S.1
Knöpfel, T.F.2
Zarotti, P.3
Ichikawa, T.4
Boyall, D.5
Carreira, E.M.6
-
37
-
-
66149109902
-
-
B.M. Trost, and A.H. Weiss Adv. Synth. Catal. 351 2009 963 For examples of enantioselective conjugate alkynylation of enones, see:
-
(2009)
Adv. Synth. Catal.
, vol.351
, pp. 963
-
-
Trost, B.M.1
Weiss, A.H.2
-
42
-
-
38949195266
-
-
T. Nishimura, X.-X. Guo, N. Uchiyama, T. Katoh, and T. Hayashi J. Am. Chem. Soc. 130 2008 1576
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 1576
-
-
Nishimura, T.1
Guo, X.-X.2
Uchiyama, N.3
Katoh, T.4
Hayashi, T.5
-
44
-
-
74949105179
-
-
O.V. Larionov, and E.J. Corey Org. Lett. 12 2010 300 For an example of rhodium-catalyzed enantioselective conjugate alkynylation of enals, see:
-
(2010)
Org. Lett.
, vol.12
, pp. 300
-
-
Larionov, O.V.1
Corey, E.J.2
-
45
-
-
70349988546
-
-
T. Nishimura, T. Sawano, and T. Hayashi Angew. Chem., Int. Ed. 48 2009 8057 For the example of rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones, see:
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 8057
-
-
Nishimura, T.1
Sawano, T.2
Hayashi, T.3
-
46
-
-
36448967496
-
-
T. Nishimura, T. Katoh, K. Takatsu, R. Shintani, and T. Hayashi J. Am. Chem. Soc. 129 2007 14158 For the example of organocatalytic formal alkynylation of enals, see:
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 14158
-
-
Nishimura, T.1
Katoh, T.2
Takatsu, K.3
Shintani, R.4
Hayashi, T.5
-
47
-
-
68049134427
-
-
M. Nielsen, C.B. Jacobsen, M.W. Paixão, N. Holub, and K.A. Jørgensen J. Am. Chem. Soc. 131 2009 10581
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 10581
-
-
Nielsen, M.1
Jacobsen, C.B.2
Paixão, M.W.3
Holub, N.4
Jørgensen, K.A.5
-
48
-
-
77955681352
-
-
A variety of other chiral ligands and metals including copper, rhodium and lithium were also evaluated and gave lower yield and enantioselectivity.
-
A variety of other chiral ligands and metals including copper, rhodium and lithium were also evaluated and gave lower yield and enantioselectivity.
-
-
-
-
49
-
-
77955701019
-
-
3N.
-
3N.
-
-
-
-
50
-
-
77955683511
-
-
For similar zinc species see:
-
For similar zinc species see:
-
-
-
-
54
-
-
0032572098
-
-
M. Uchiyama, M. Kameda, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo, and T. Sakamoto J. Am. Chem. Soc. 120 1998 4934
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4934
-
-
Uchiyama, M.1
Kameda, M.2
Mishima, O.3
Yokoyama, N.4
Koike, M.5
Kondo, Y.6
Sakamoto, T.7
-
55
-
-
0033105506
-
-
L. Tan, C. Chen, R.D. Tillyer, E.J.J. Grabowski, and P.J. Reider Angew. Chem., Int. Ed. 38 1999 711
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 711
-
-
Tan, L.1
Chen, C.2
Tillyer, R.D.3
Grabowski, E.J.J.4
Reider, P.J.5
-
57
-
-
77955672933
-
-
Zincate is depicted as a monomer for clarity. Preliminary NMR studies indicate that several different zincate species exist in solution.
-
Zincate is depicted as a monomer for clarity. Preliminary NMR studies indicate that several different zincate species exist in solution.
-
-
-
-
58
-
-
77955707793
-
-
For full details, see Ref. 4.
-
For full details, see Ref. 4.
-
-
-
-
59
-
-
77955666538
-
-
Other solvents (Me-THF, MTBE, DME, toluene) evaluated provided lower ee (<80%) and yield (<90%);
-
Other solvents (Me-THF, MTBE, DME, toluene) evaluated provided lower ee (<80%) and yield (<90%);
-
-
-
-
60
-
-
77955695510
-
-
2Zn were equally efficient;
-
2Zn were equally efficient;
-
-
-
-
61
-
-
77955695509
-
-
Enantioselectivity was not dependent on the concentration (0.04-0.2 M);
-
Enantioselectivity was not dependent on the concentration (0.04-0.2 M);
-
-
-
-
62
-
-
77955702813
-
-
2Zn/trifluoroethanol/cinchonidine) had no effect.
-
2Zn/trifluoroethanol/cinchonidine) had no effect.
-
-
-
-
63
-
-
3042654141
-
-
S.D. Walker, T.E. Barder, J.R. Martinelli, and S.L. Buchwald Angew. Chem., Int. Ed. 43 2004 1871
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1871
-
-
Walker, S.D.1
Barder, T.E.2
Martinelli, J.R.3
Buchwald, S.L.4
|