-
1
-
-
0033617465
-
-
(a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 3322-3327
-
-
Myers, A.G.1
Schnider, P.2
Kwon, S.3
Kung, D.W.4
-
2
-
-
0030810476
-
-
(b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 6496-6511
-
-
Myers, A.G.1
Yang, B.H.2
Chen, H.3
McKinstry, L.4
Kopecky, D.J.5
Gleason, J.L.6
-
3
-
-
0031047509
-
-
(c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 656-673
-
-
Myers, A.G.1
Gleason, J.L.2
Yoon, T.3
Kung, D.W.4
-
6
-
-
0029126361
-
-
(f) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 8488-8489
-
-
Myers, A.G.1
Gleason, J.L.2
Yoon, T.3
-
7
-
-
0027960624
-
-
(g) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 9361-9362
-
-
Myers, A.G.1
Yang, B.H.2
Chen, H.3
Gleason, J.L.4
-
8
-
-
0037458599
-
-
(a) Vicario, J. L.; Badía, D.; Carrillo, L. Tetrahedron: Asymmetry 2003, 14, 489-495.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 489-495
-
-
Vicario, J.L.1
Badía, D.2
Carrillo, L.3
-
9
-
-
0034674548
-
-
(b) Vicario, J. L.; Badia, D.; Domínguez, E.; Rodríguez, M.; Carrillo, L. J. Org. Chem. 2000, 65, 3754-3760.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3754-3760
-
-
Vicario, J.L.1
Badia, D.2
Domínguez, E.3
Rodríguez, M.4
Carrillo, L.5
-
10
-
-
0035966165
-
-
(a) Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030-9032.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 9030-9032
-
-
Vicario, J.L.1
Badía, D.2
Carrillo, L.3
-
11
-
-
0035826373
-
-
(b) Vicario, J. L.; Badía, D.; Carrillo, L. Org. Lett. 2001, 3, 773-776.
-
(2001)
Org. Lett.
, vol.3
, pp. 773-776
-
-
Vicario, J.L.1
Badía, D.2
Carrillo, L.3
-
12
-
-
0035178037
-
-
(a) Anakabe, E.; Vicario, J. L.; Badía, D.; Carrillo, L.; Yoldi, V. Eur. J. Org. Chem. 2001, 4343-4352.
-
(2001)
Eur. J. Org. Chem.
, pp. 4343-4352
-
-
Anakabe, E.1
Vicario, J.L.2
Badía, D.3
Carrillo, L.4
Yoldi, V.5
-
13
-
-
0033600688
-
-
(b) Vicario, J. L.; Badia, D.; Domínguez, E.; Crespo, A.; Carrillo, L.; Anakabe, E. Tetrahedron Lett. 1999, 40, 7123-7126.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 7123-7126
-
-
Vicario, J.L.1
Badia, D.2
Domínguez, E.3
Crespo, A.4
Carrillo, L.5
Anakabe, E.6
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14
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1642367602
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note
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Enolates of glycinamides exhibited lower selectivity in the absence of LiCl. See ref 1c.
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15
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0037433275
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For examples, see: (a) Duffey, M. O.; Le Tiran, A.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 1458-1459.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1458-1459
-
-
Duffey, M.O.1
Le Tiran, A.2
Morken, J.P.3
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18
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0037198780
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Smitrovich, J. H.; Boice, G. N.; Qu, C.; DiMichele, L.; Nelson, T. D.; Huffman, M. A.; Murry, J.; McNamara, J.; Reider, P. J. Org. Lett. 2002, 4, 1963-1966.
-
(2002)
Org. Lett.
, vol.4
, pp. 1963-1966
-
-
Smitrovich, J.H.1
Boice, G.N.2
Qu, C.3
DiMichele, L.4
Nelson, T.D.5
Huffman, M.A.6
Murry, J.7
McNamara, J.8
Reider, P.J.9
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19
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0032977667
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For the use of other chiral auxiliaries on the Michael donor, see: (a) Enders, D.; Teschner, P.; Gröbner, R.; Raabe, G. Synthesis 1999, 237-242.
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(1999)
Synthesis
, pp. 237-242
-
-
Enders, D.1
Teschner, P.2
Gröbner, R.3
Raabe, G.4
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20
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0029026897
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(b) Kanemasa, S.; Nomura, M.; Yoshinaga, S.; Yamamoto, H. Tetrahedron 1995, 51, 10463-10476.
-
(1995)
Tetrahedron
, vol.51
, pp. 10463-10476
-
-
Kanemasa, S.1
Nomura, M.2
Yoshinaga, S.3
Yamamoto, H.4
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21
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0000504848
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(c) Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D. ; Kato, Y. J. Org. Chem. 1991, 56, 5750-5752.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5750-5752
-
-
Evans, D.A.1
Bilodeau, M.T.2
Somers, T.C.3
Clardy, J.4
Cherry, D.5
Kato, Y.6
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22
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0000075786
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(d) Yamaguchi, M.; Hasebe, K.; Tanaka, S.; Minami, T. Tetrahedron Lett. 1986, 27, 959-962.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 959-962
-
-
Yamaguchi, M.1
Hasebe, K.2
Tanaka, S.3
Minami, T.4
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23
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0034826462
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While this work was in progress, Myers et al. reported the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to a nitroalkene and vinyl sulfoxide with modest selectivities and yields. See: Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7207-7219
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-
Myers, A.G.1
Barbay, J.K.2
Zhong, B.3
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24
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1642352923
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note
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In contrast, the alkylation requires the presence of 6 equiv of LiCl to increase conversion and the rate of alkylation. See ref 1b.
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25
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0030909045
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Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633-2636.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 2633-2636
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Kress, M.H.1
Yang, C.2
Yasuda, N.3
Grabowski, E.J.J.4
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28
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0000877113
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We found that the presence of 5-10 mol % water is crucial for reproducibility. See: Sunitha, K.; Balasubramanian, K. K. Tetrahedron 1987, 43, 3269-3278.
-
(1987)
Tetrahedron
, vol.43
, pp. 3269-3278
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-
Sunitha, K.1
Balasubramanian, K.K.2
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29
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1642268488
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note
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The stereochemistry at the epimerizable stereocenter of 5 has not been determined.
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30
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0001114359
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For the Michael addition of N,N-disubstituted amide enolates with α,β-unsaturated ketones, see: Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132-157.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 132-157
-
-
Oare, D.A.1
Henderson, M.A.2
Sanner, M.A.3
Heathcock, C.H.4
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31
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0001161387
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A reversal in the facial selectivity in the alkylation of prolinol amide enolates with alkyl halides and epoxides was observed by Askin et al., who proposed that the lithium alkoxide of the auxiliary directs the approach of the epoxide to rationalize this observation. See: Askin, D.; Volante, R. P.; Ryan, K. M.; Reamer, R. A.; Shinkai, I. Tetrahedron Lett. 1988, 29, 4245-4248.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 4245-4248
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Askin, D.1
Volante, R.P.2
Ryan, K.M.3
Reamer, R.A.4
Shinkai, I.5
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32
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1642346394
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note
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Synclinal orientation of the Michael acceptor is considered on the basis of analogy to the stereochemical rationale proposed by Oare et al. for the addition of lithium enolates of amides and thioamides to α,β -unsaturated ketones (ref 16). The formation of anti-3 through an open transition state E is also possible.
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33
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1642320498
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note
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Although the 3,4-difluoro analogue 1c was examined as well, and generated similar results, a single representative reaction using 1a will be our focus.
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34
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1642393493
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note
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1H spectrum revealed that the remaining portion of the reaction is made up of broadened species which may be attributed to partial aggregation.
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35
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84990085779
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For a review on the structure and reactivity of lithium enolates, see: Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
-
(1988)
Angew. Chem., Int. Ed. Engl.
, vol.27
, pp. 1624-1654
-
-
Seebach, D.1
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36
-
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0029966049
-
-
Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339-1347.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1339-1347
-
-
Henderson, K.W.1
Dorigo, A.E.2
Liu, Q.-Y.3
Williard, P.G.4
Schleyer, P.V.R.5
Bernstein, P.R.6
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37
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0028136779
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Tanner, D.; Birgersson, C.; Gogoll, A. Tetrahedron 1994, 50, 9797-9824.
-
(1994)
Tetrahedron
, vol.50
, pp. 9797-9824
-
-
Tanner, D.1
Birgersson, C.2
Gogoll, A.3
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