-
1
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-
0002923489
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-
For reviews, see: a) R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-56;
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Bull. Chem. Soc. Jpn.
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Noyori, R.1
Tokunaga, M.2
Kitamura, M.3
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3
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57249106473
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-
c) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321-331;
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Chem. Soc. Rev.
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, pp. 321-331
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-
Huerta, F.F.1
Minidis, A.B.E.2
Bäckvall, J.-E.3
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5
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-
27544465688
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-
Ref. [1]
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For representative stereomutative examples, see: a) Ref. [1];
-
-
-
-
6
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-
0000687774
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-
(Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York
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b) A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 833-884;
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(1999)
Comprehensive Asymmetric Catalysis, Vol. 2
, vol.2
, pp. 833-884
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-
Pfaltz, A.1
Lautens, M.2
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7
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0034725412
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-
c) B. M. Trost, R. C. Bunt, R. C. Lemoine, T. L. Calkins, J. Am. Chem. Soc. 2000, 122, 5968-5976.
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J. Am. Chem. Soc.
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-
Trost, B.M.1
Bunt, R.C.2
Lemoine, R.C.3
Calkins, T.L.4
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8
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-
27544509748
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-
note
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The term stereoablation describes the conversion of a chiral molecule to an achiral molecule (e.g., Figure 1, pathway II, (±)-A→C). Ablation from the Oxford English Dictionary meaning "the action or process of carrying away or removing; removal".
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-
-
-
9
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0037138675
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For representative stereoablative examples, see: a) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268;
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J. Am. Chem. Soc.
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Hamada, T.1
Chieffi, A.2
Åhman, J.3
Buchwald, S.L.4
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10
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6044224571
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b) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474-2477;
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Angew. Chem.
, vol.116
, pp. 2474-2477
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Mase, N.1
Tanaka, F.2
Barbas III, C.F.3
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11
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3042625080
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Angew. Chem. Int. Ed. 2004, 43, 2420-2423;
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(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 2420-2423
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-
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13
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19744363827
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d) D. Magdziak, G. Lalic, H. M. Lee, K. C. Fortner, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2005, 127, 7284-7285.
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Magdziak, D.1
Lalic, G.2
Lee, H.M.3
Fortner, K.C.4
Aloise, A.D.5
Shair, M.D.6
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14
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-
27544460434
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-
note
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To the best of our knowledge, there are no examples of the catalytic asymmetric synthesis of quaternary carbon stereocenters from racemates with quaternary stereocenters.
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-
-
-
15
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27544442015
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A diastereoselective example of such a process has been recently reported, see: K. Xu, G. Lalic, S. M. Sheehan, M. D. Shair, Angew. Chem. 2005, 117, 2299-2301;
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(2005)
Angew. Chem.
, vol.117
, pp. 2299-2301
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Xu, K.1
Lalic, G.2
Sheehan, S.M.3
Shair, M.D.4
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16
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17644373114
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Angew. Chem. Int. Ed. 2005, 44, 2259-2261.
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(2005)
Angew. Chem. Int. Ed.
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, pp. 2259-2261
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21
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0000273585
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and references therein
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b) J. M. J. Williams, Synlett 1996, 705-710, and references therein.
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(1996)
Synlett
, pp. 705-710
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Williams, J.M.J.1
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22
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14844303302
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Subsequent to our initial report, a similar transformation using a bisphosphine ligand was reported, see: B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847.
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(2005)
J. Am. Chem. Soc.
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, pp. 2846-2847
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Trost, B.M.1
Xu, J.2
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23
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11844283363
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An elegant alternative catalytic asymmetric alkylation of cyclic ketones for the synthesis of quaternary stereocenters has been recently described, see: A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 62-63.
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(2005)
J. Am. Chem. Soc.
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Doyle, A.G.1
Jacobsen, E.N.2
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24
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27544503368
-
-
See Supporting Information for details
-
See Supporting Information for details.
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-
-
-
25
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0011446373
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This hypothesis has been experimentally supported for non-enantioselective systems, see: a) J. Tsuji, T. Yamada, I. Minami, M. Yuhara, M. Nisar, I. Shimizu, J. Org. Chem. 1987, 52, 2988-2995;
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Tsuji, J.1
Yamada, T.2
Minami, I.3
Yuhara, M.4
Nisar, M.5
Shimizu, I.6
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26
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4644282162
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b) J.-F. Detalle, A. Riahi, V. Steinmetz, F. Hénin, J. Muzart, J. Org. Chem. 2004, 69, 6528-6532.
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-
Detalle, J.-F.1
Riahi, A.2
Steinmetz, V.3
Hénin, F.4
Muzart, J.5
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27
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18744415432
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For an excellent review on metal-catalyzed decarboxylation, see: J. A. Tunge, E. C. Burger, Eur. J. Org. Chem. 2005, 9, 1715-1726.
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(2005)
Eur. J. Org. Chem.
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Tunge, J.A.1
Burger, E.C.2
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31
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0242574862
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b) R. Sarpong, J. T. Su, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 13624-13625.
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Sarpong, R.1
Su, J.T.2
Stoltz, B.M.3
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32
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27544497378
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note
-
3 was used as the ligand for the conversion of (±)-13 into (±)-14 and the meso isomer of 14 (not shown), a diastereomeric ratio of 70:30 was observed.
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