-
1
-
-
34247362490
-
-
For a review, see: C. M. Goodman, S. Choi, S. Shandler, W. F. DeGrado, Nat. Chem. Biol. 2007, 3, 252.
-
(2007)
Nat. Chem. Biol.
, vol.3
, pp. 252
-
-
Goodman, C.M.1
Choi, S.2
Shandler, S.3
Degrado, W.F.4
-
2
-
-
38349100690
-
-
For a review, see: M. Santanu, J. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
-
(2007)
Chem. Rev.
, vol.107
, pp. 5471
-
-
Santanu, M.1
Yang, J.2
Hoffmann, S.3
List, B.4
-
3
-
-
33846601028
-
-
B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 768
-
-
Wang, B.1
Wu, F.2
Wang, Y.3
Liu, X.4
Deng, L.5
-
4
-
-
44049101018
-
-
a) T. A. Moss, A. Alba, D. Hepworth, D. J. Dixon, Chem. Commun. 2008, 2474;
-
(2008)
Chem. Commun.
, pp. 2474
-
-
Moss, T.A.1
Alba, A.2
Hepworth, D.3
Dixon, D.J.4
-
5
-
-
48749115535
-
-
b) T. A. Moss, D. R. Fenwick, D.J. Dixon, J. Am. Chem. Soc. 2008, 130, 10076.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 10076
-
-
Moss, T.A.1
Fenwick, D.R.2
Dixon, D.J.3
-
6
-
-
52149091728
-
-
For a related study, see: c
-
For a related study, see: c) M. W. Paixão, M. Nielsen, C. B. Jacobsen, K. A. Jørgensen, Org. Biomol. Chem. 2008, 6, 3467.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 3467
-
-
Paixão, M.W.1
Nielsen, M.2
Jacobsen, C.B.3
Jørgensen, K.A.4
-
7
-
-
36448966780
-
-
For examples of azetidinium ions used as electrophiles with carbon nucleophiles, see
-
For examples of azetidinium ions used as electrophiles with carbon nucleophiles, see: F. Couty, O. David, B. Drouillat, Tetrahedron Lett. 2007, 48, 9180.
-
(2007)
Tetrahedron Lett.
, vol.48
, pp. 9180
-
-
Couty, F.1
David, O.2
Drouillat, B.3
-
8
-
-
0037424821
-
-
For a comprehensive review on the synthesis and reactions of cyclic sulfamidates, see
-
For a comprehensive review on the synthesis and reactions of cyclic sulfamidates, see: R. E. Melendez, W. D. Lubell, Tetrahedron 2003, 59, 2581.
-
(2003)
Tetrahedron
, vol.59
, pp. 2581
-
-
Melendez, R.E.1
Lubell, W.D.2
-
9
-
-
0025648320
-
-
For seminal work in this area, see: a
-
For seminal work in this area, see: a) J. E. Baldwin, A. C. Spivey, C. J. Schofield, Tetrahedron: Asymmetry 1990, 1, 881;
-
(1990)
Tetrahedron: Asymmetry
, vol.1
, pp. 881
-
-
Baldwin, J.E.1
Spivey, A.C.2
Schofield, C.J.3
-
10
-
-
0026475477
-
-
b) G. F. Cooper, K. E. McCarthy, M. G. Martin, Tetrahedron Lett. 1992, 33, 5895;
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 5895
-
-
Cooper, G.F.1
McCarthy, K.E.2
Martin, M.G.3
-
12
-
-
33746389227
-
-
d) L. T. Boulton, H. T. Stock, J. Raphy, D. C. Horwell, J. Chem. Soc. Perkin Trans. 1 1999, 1421;
-
(1999)
J. Chem. Soc. Perkin Trans. 1
, pp. 1421
-
-
Boulton, L.T.1
Stock, H.T.2
Raphy, J.3
Horwell, D.C.4
-
15
-
-
11444250543
-
-
For synthetic procedures, see: a
-
For synthetic procedures, see: a) J. F. Bower, J. Svenda, A.J. Williams, J. P. H. Charmant, R. M. Lawrence, P. Szeto, T. Gallagher, Org. Lett. 2004, 6, 4727;
-
(2004)
Org. Lett.
, vol.6
, pp. 4727
-
-
Bower, J.F.1
Svenda, J.2
Williams, A.J.3
Charmant, J.P.H.4
Lawrence, R.M.5
Szeto, P.6
Gallagher, T.7
-
16
-
-
36348990855
-
-
b) J. F. Bower, P. Szeto, T. Gallagher, Org. Lett. 2007, 9, 4909;
-
(2007)
Org. Lett.
, vol.9
, pp. 4909
-
-
Bower, J.F.1
Szeto, P.2
Gallagher, T.3
-
17
-
-
33646716662
-
-
c) J. F. Bower, S. Chakthong, J. Svenda, A. J. Williams, R. M. Lawrence, P. Szeto, T. Gallagher, Org. Biomol. Chem 2006, 4, 1868;
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 1868
-
-
Bower, J.F.1
Chakthong, S.2
Svenda, J.3
Williams, A.J.4
Lawrence, R.M.5
Szeto, P.6
Gallagher, T.7
-
18
-
-
34547587015
-
-
d) J. F. Bower, A. J. Williams, H. L. Woodward, P. Szeto, R. M. Lawrence, T. Gallagher, Org. Biomol. Chem. 2007, 5, 2636.
-
(2007)
Org. Biomol. Chem.
, vol.5
, pp. 2636
-
-
Bower, J.F.1
Williams, A.J.2
Woodward, H.L.3
Szeto, P.4
Lawrence, R.M.5
Gallagher, T.6
-
19
-
-
33846907785
-
-
For synthetic applications, see: a
-
For synthetic applications, see: a) J. F. Bower, T. Riis-Johannessen, P. Szeto, A. J. Whitehead, T. Gallagher, Chem. Commun. 2007, 728;
-
(2007)
Chem. Commun.
, pp. 728
-
-
Bower, J.F.1
Riis-Johannessen, T.2
Szeto, P.3
Whitehead, A.J.4
Gallagher, T.5
-
26
-
-
33845470711
-
-
For selected reports of phase-transfer-catalyzed alkylations forming a quaternary stereocenter, see: a
-
For selected reports of phase-transfer-catalyzed alkylations forming a quaternary stereocenter, see: a) U. H. Dolling, P. Davis, E.J.J. Grabowski, J. Am. Chem. Soc. 1984, 106, 466;
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 466
-
-
Dolling, U.H.1
Davis, P.2
Grabowski, E.J.J.3
-
28
-
-
33746310158
-
-
c) S.-S. Jew, Y.-J. Lee, J. Lee, M. J. Kang, B.-S. Jeong, J.-H. Lee, M-S. Yoo, M-J. Kim, S.-h. Choi, J.-M. Ku, H.-g. Park, Angew. Chem. 2004, 116, 2436;
-
(2004)
Angew. Chem.
, vol.116
, pp. 2436
-
-
Jew, S.-S.1
Lee, Y.-J.2
Lee, J.3
Kang, M.J.4
Jeong, B.-S.5
Lee, J.-H.6
Yoo, M.-S.7
Kim, M.-J.8
Choi, S.-H.9
Ku, J.-M.10
Park, H.-G.11
-
30
-
-
3042767126
-
-
d) T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem 2003, 115, 3926;
-
(2003)
Angew. Chem
, vol.115
, pp. 3926
-
-
Ooi, T.1
Miki, T.2
Taniguchi, M.3
Shiraishi, M.4
Takeuchi, M.5
Maruoka, K.6
-
32
-
-
4644351571
-
-
e) E. J. Park, M. H. Kim, D. Y. Kim, J. Org. Chem. 2004, 69, 6897;
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6897
-
-
Park, E.J.1
Kim, M.H.2
Kim, D.Y.3
-
33
-
-
53249153070
-
-
f) T. Ooi, K. Fukumoto, K. Maruoka, Angew. Chem. 2006, 118, 3923;
-
(2006)
Angew. Chem.
, vol.118
, pp. 3923
-
-
Ooi, T.1
Fukumoto, K.2
Maruoka, K.3
-
35
-
-
70349978850
-
-
g) D. Uraguchi, Y. Asai, T. Ooi, Angew. Chem. 2009, 121, 747;
-
(2009)
Angew. Chem.
, vol.121
, pp. 747
-
-
Uraguchi, D.1
Asai, Y.2
Ooi, T.3
-
37
-
-
33846220324
-
-
a) T. B. Poulsen, L. Bernardi, J. Aleman, J. Overgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 441;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 441
-
-
Poulsen, T.B.1
Bernardi, L.2
Aleman, J.3
Overgaard, J.4
Jørgensen, K.A.5
-
38
-
-
34247853260
-
-
b) L. Bernardi, J. L. Cantarero, B. Neiss, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 5772;
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 5772
-
-
Bernardi, L.1
Cantarero, J.L.2
Neiss, B.3
Jørgensen, K.A.4
-
39
-
-
74549141529
-
-
c) T. B. Poulsen, L. Bernardi, M. Bell, K. A. Jørgeniesi, Angew. Chem. 2006, 118, 6101;
-
(2006)
, Angew. Chem.
, vol.118
, pp. 6101
-
-
Poulsen, T.B.1
Bernardi, L.2
Bell, M.3
Jørgeniesi, K.A.4
-
41
-
-
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-
-
CCDC 753701 (3d) and 753702 (5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via
-
CCDC 753701 (3d) and 753702 (5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif.
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74549174131
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Subjection of acyclic pro-nucleophile tert-butyl-2-methylacetoacetate to our optimal conditions resulted in a 2:3 inseparable mixture of O- and C-alkylated products, respectively.
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Subjection of acyclic pro-nucleophile tert-butyl-2-methylacetoacetate to our optimal conditions resulted in a 2:3 inseparable mixture of O- and C-alkylated products, respectively.
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43
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74549140934
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The stereochemistry of indanone adducts 3 b, 3 c, 3e-3h were assigned by analogy to compound 3d (absolute configuration determined by X-ray crystallography). Compounds 3j and 31 were assigned by analogy to the cyclopentanone system (see Ref. [13c]). Succinimide products 3i and 3m were assigned by analogy to compound 5 c in the matched system with (S)-1f and catalyst 4a (relative configuration determined by X-ray crystallography). Glutarimide adducts 3a and 3k were assigned by analogy to the succinimide, and cyclohexanone systems (Ref. [13]).
-
The stereochemistry of indanone adducts 3 b, 3 c, 3e-3h were assigned by analogy to compound 3d (absolute configuration determined by X-ray crystallography). Compounds 3j and 31 were assigned by analogy to the cyclopentanone system (see Ref. [13c]). Succinimide products 3i and 3m were assigned by analogy to compound 5 c in the matched system with (S)-1f and catalyst 4a (relative configuration determined by X-ray crystallography). Glutarimide adducts 3a and 3k were assigned by analogy to the succinimide, and cyclohexanone systems (Ref. [13]).
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44
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74549132544
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Acyclic ethyl phenylcyanoacetate gave product 5e with (S)-1f and 4a (10 mol%) in an 84% yield and 3:2 d.r. (see the Supporting Information).
-
Acyclic ethyl phenylcyanoacetate gave product 5e with (S)-1f and 4a (10 mol%) in an 84% yield and 3:2 d.r. (see the Supporting Information).
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45
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35549006377
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An electrophile-directed diastereoselective alkylation has recently been described
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An electrophile-directed diastereoselective alkylation has recently been described: S. P. Marsden, R. Newton, J. Am. Chem. Soc. 2007, 129, 12600.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12600
-
-
Marsden, S.P.1
Newton, R.2
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46
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74549114251
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When the reaction was conducted with racemic 1g, a 1:1 mixture of diastereomers was obtained (see the Supporting Information)
-
When the reaction was conducted with racemic 1g, a 1:1 mixture of diastereomers was obtained (see the Supporting Information).
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