-
1
-
-
0001924336
-
-
(a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
-
(1982)
Top. Stereochem.
, vol.13
, pp. 1-115
-
-
Evans, D.A.1
Nelson, J.V.2
Taber, T.R.3
-
3
-
-
0021775497
-
-
(c) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30.
-
(1985)
Angew. Chem., Int. Ed. Engl.
, vol.24
, pp. 1-30
-
-
Masamune, S.1
Choy, W.2
Petersen, J.S.3
Sita, L.R.4
-
4
-
-
0000584420
-
-
Morrison, J. D., Ed.; Academic Press: Orlando, FL
-
(d) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, pp 111-212.
-
(1984)
Asymmetric Synthesis
, vol.3
, pp. 111-212
-
-
Heathcock, C.H.1
-
6
-
-
0003417469
-
-
Pergamon Press: Oxford
-
(f) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
-
-
Trost, B.M.1
Fleming, I.2
Winterfeldt, E.3
-
7
-
-
0001769274
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(g) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 99-131.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 99-131
-
-
Mekelburger, H.B.1
Wilcox, C.S.2
-
8
-
-
0000851696
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(h) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 133-179,181-238.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 133-179
-
-
Heathcock, C.H.1
-
9
-
-
0001091186
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(i) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 239-275.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 239-275
-
-
Kim, B.M.1
Williams, S.F.2
Masamune, S.3
-
10
-
-
0000144592
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(j) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 277-299.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 277-299
-
-
Rathke, M.W.1
Weipert, P.2
-
11
-
-
0001653533
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(k) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 301-319.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 301-319
-
-
Paterson, I.1
-
13
-
-
0000922736
-
-
Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
-
(m) Braun, M. In Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp 1603-1666, 1713-1735.
-
(1996)
Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis
, vol.3
, pp. 1603-1666
-
-
Braun, M.1
-
14
-
-
0001196589
-
-
(n) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
-
(1999)
Chem. Rev.
, vol.99
, pp. 1095-1120
-
-
Mahrwald, R.1
-
15
-
-
0037016618
-
-
(o) Palomo, C.; Oiarbide, M.; García, J. M. Chem.-Eur. J. 2002, 8, 36-44.
-
(2002)
Chem.-Eur. J.
, vol.8
, pp. 36-44
-
-
Palomo, C.1
Oiarbide, M.2
García, J.M.3
-
16
-
-
1642386775
-
-
(p) Palomo, C.; Oiarbide, M.; García, J. M. Chem. Soc. Rev. 2004, 33, 65-75.
-
(2004)
Chem. Soc. Rev.
, vol.33
, pp. 65-75
-
-
Palomo, C.1
Oiarbide, M.2
García, J.M.3
-
19
-
-
0034695654
-
-
(a) Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron 2000, 56, 677-683.
-
(2000)
Tetrahedron
, vol.56
, pp. 677-683
-
-
Carda, M.1
Murga, J.2
Falomir, E.3
González, F.4
Marco, J.A.5
-
20
-
-
0037206821
-
-
(b) Murga, J.; Falomir, E.; Carda, M.; Marco, J. A. Tetrahedron: Asymmetry 2002, 13, 2317-2327.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 2317-2327
-
-
Murga, J.1
Falomir, E.2
Carda, M.3
Marco, J.A.4
-
21
-
-
0037175549
-
-
(c) Murga, J.; Falomir, E.; González, F.; Carda, M.; Marco, J. A. Tetrahedron 2002, 58, 9697-9707.
-
(2002)
Tetrahedron
, vol.58
, pp. 9697-9707
-
-
Murga, J.1
Falomir, E.2
González, F.3
Carda, M.4
Marco, J.A.5
-
22
-
-
14844336872
-
-
3 synthon of ketone 1 is conceptually related to dihydroxyacetone enolates. See: Enders, D.; Voith, M.; Lenzen, A. Angew. Chem., Int. Ed. 2005, 44, 1304-1325.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 1304-1325
-
-
Enders, D.1
Voith, M.2
Lenzen, A.3
-
23
-
-
0034637186
-
-
Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron: Asymmetry 2000, 11, 3211-3220.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 3211-3220
-
-
Carda, M.1
Murga, J.2
Falomir, E.3
González, F.4
Marco, J.A.5
-
24
-
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0001349560
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This stereochemical outcome of aldol reactions mediated by dicyclohexylboron chloride may be general in α-oxygenated ketones: Murga, J.; Falomir, E.; Carda, M.; González, F.; Marco, J. A. Org. Lett. 2001, 3, 901-904.
-
(2001)
Org. Lett.
, vol.3
, pp. 901-904
-
-
Murga, J.1
Falomir, E.2
Carda, M.3
González, F.4
Marco, J.A.5
-
28
-
-
0037122039
-
-
(d) Yeung, K.-S.; Paterson, I. Angew. Chem., Int. Ed. 2002, 41, 4632-4653.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4632-4653
-
-
Yeung, K.-S.1
Paterson, I.2
-
30
-
-
0142258961
-
-
Marco, J. A.; Carda, M.; Díaz-Oltra, S.; Murga, J.; Falomir, E.; Roeper, H. J. Org. Chem. 2003, 68, 8577-8582.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 8577-8582
-
-
Marco, J.A.1
Carda, M.2
Díaz-Oltra, S.3
Murga, J.4
Falomir, E.5
Roeper, H.6
-
31
-
-
25444513893
-
-
note
-
7 we assumed that the not isolated, minor stereoisomer was the "anti-Felkin" stereoisomer, which resulted from attack to the aldehyde Si face. However, we later found that aldehyde 5b is much more prone to racemization than its analogue 5a. We thus believe that the minor stereoisomer, which appears in the reaction mixture in variable proportions, is formed from the small proportion of the undesired enantiomer, generated adventitiously during the synthesis and isolation of the aldehyde. The preparation of aldehydes 5 has to be performed with extreme care, to keep racemization to a minimum (the results presented in this paper and in refs 7 and 9 are part of the Ph.D. thesis of S.D.-O., Universidad Jaume I, July 2005).
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-
-
32
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1542298882
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The methodology described in ref 7 has been applied to the stereoselective synthesis of the natural lactone anamarine: Díaz-Oltra, S.; Murga, J.; Falomir, E.; Carda, M.; Marco, J. A. Tetrahedron 2004, 60, 2979-2985.
-
(2004)
Tetrahedron
, vol.60
, pp. 2979-2985
-
-
Díaz-Oltra, S.1
Murga, J.2
Falomir, E.3
Carda, M.4
Marco, J.A.5
-
33
-
-
49949128203
-
-
(a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199-2204.
-
(1968)
Tetrahedron Lett.
, vol.9
, pp. 2199-2204
-
-
Chérest, M.1
Felkin, H.2
Prudent, N.3
-
36
-
-
0036678859
-
-
See also, however: Smith, R. J.; Trzoss, M.; Bühl, M.; Bienz, S. Eur. J. Org. Chem. 2002, 2770-2775.
-
(2002)
Eur. J. Org. Chem.
, pp. 2770-2775
-
-
Smith, R.J.1
Trzoss, M.2
Bühl, M.3
Bienz, S.4
-
37
-
-
0037541165
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-
Shortly before we concluded our investigation with ketone 1, a paper by Evans and co-workers appeared in which the Cornforth model was resurrected to provide a good explanation of the sterochemical outcome of aldol reactions of achiral ketones with α-heteroatom-substituted aldehydes: Evans, D. A.; Siska, S. J.; Cee, V. J. Angew. Chem., Int. Ed. 2003, 42, 1761-1765.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1761-1765
-
-
Evans, D.A.1
Siska, S.J.2
Cee, V.J.3
-
38
-
-
0001584981
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-
Cornforth's model has been previously applied to reactions of α-oxygenated aldehydes with achiral allylboron compounds: (a) Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem. Soc. 1986, 108, 3422-3434.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3422-3434
-
-
Roush, W.R.1
Adam, M.A.2
Walts, A.E.3
Harris, D.J.4
-
41
-
-
0035956406
-
-
(d) The higher stability of Cornforth-like transition structures in some additions of allylboron reagents to α-oxygenated aldehydes has also received theoretical support: Gung, B. W.; Xue, X. Tetrahedron: Asymmetry 2001, 12, 2955-2959.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 2955-2959
-
-
Gung, B.W.1
Xue, X.2
-
42
-
-
0002446724
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(e) For more detailed accounts of the diastereoselective reactions of allylboron compounds, see: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 1-54.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 1-54
-
-
Roush, W.R.1
-
43
-
-
0000094579
-
-
Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, and references therein
-
Roush, W. R. In Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp 1410-1486, and references therein.
-
(1996)
Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis
, vol.3
, pp. 1410-1486
-
-
Roush, W.R.1
-
44
-
-
0001137591
-
-
(f) For a related situation in the addition of an allenylstannane, see: Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 3211-3213
-
-
Marshall, J.A.1
Wang, X.-J.2
-
45
-
-
25444504699
-
-
note
-
7 Because aldehydes 6c gave essentially the same results as 6b in aldol reactions with 1, only the latter were used in the present work.
-
-
-
-
46
-
-
25444491118
-
-
note
-
17 Standard manipulations of the protecting groups further permitted the preparation of other cyclic derivatives suitable for similar NMR studies. Descriptions of these chemical correlations and analytical data for correlation products are given in the Supporting Information.
-
-
-
-
47
-
-
25444498185
-
-
note
-
The stereostructures of two correlation compounds related to aldols 10a and 11a (see Supporting Information) were established by means of X-ray diffraction analyses. Crystallographic data (excluding structure factors) have been deposited at the Cambridge Crystallographic Data Center as supplementary material with references CCDC-269222 and CCDC-269772. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax, +44(0)-1223-336033 or e-mail, deposit@ ccdc.cam.ac.uk].
-
-
-
-
49
-
-
0001951357
-
-
Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
-
(1998)
Acc. Chem. Res.
, vol.31
, pp. 9-17
-
-
Rychnovsky, S.D.1
Rogers, B.N.2
Richardson, T.I.3
-
51
-
-
0001346069
-
-
For theoretical studies on boron aldol reactions, see: (a) Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 481-493
-
-
Li, Y.1
Paddon-Row, M.N.2
Houk, K.N.3
-
52
-
-
0011464872
-
-
(b) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 3295-3303
-
-
Goodman, J.M.1
Kahn, S.D.2
Paterson, I.3
-
53
-
-
33751553232
-
-
(c) Bernardi, A.; Capelli, A. M.; Gennari, C.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1990, 55, 3576-3581.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 3576-3581
-
-
Bernardi, A.1
Capelli, A.M.2
Gennari, C.3
Goodman, J.M.4
Paterson, I.5
-
54
-
-
0026087558
-
-
(d) Bernardi, A.; Capelli, A. M.; Comotti, A.; Gennari, C.; Gardner, M.; Goodman, J. M.; Paterson, I. Tetrahedron 1991, 47, 3471-3484.
-
(1991)
Tetrahedron
, vol.47
, pp. 3471-3484
-
-
Bernardi, A.1
Capelli, A.M.2
Comotti, A.3
Gennari, C.4
Gardner, M.5
Goodman, J.M.6
Paterson, I.7
-
55
-
-
0000047490
-
-
(e) Bernardi, F.; Robb, M. A.; Suzzi-Valli, G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 6472-6475.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 6472-6475
-
-
Bernardi, F.1
Robb, M.A.2
Suzzi-Valli, G.3
Tagliavini, E.4
Trombini, C.5
Umani-Ronchi, A.6
-
56
-
-
0026643343
-
-
(f) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
-
(1992)
Tetrahedron
, vol.48
, pp. 4439-4458
-
-
Gennari, C.1
Vieth, S.2
Comotti, A.3
Vulpetti, A.4
Goodman, J.M.5
Paterson, I.6
-
57
-
-
0027444510
-
-
(g) Vulpetti, A.; Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron 1993, 49, 685-696. See also ref 3c.
-
(1993)
Tetrahedron
, vol.49
, pp. 685-696
-
-
Vulpetti, A.1
Bernardi, A.2
Gennari, C.3
Goodman, J.M.4
Paterson, I.5
-
59
-
-
0000110756
-
-
C-X orbital (for α-heteroatom-substituted aldehydes) nor is the sterically bulkiest one (for aldehydes not bearing α-heteroatoms). See also ref 20.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 3353-3361
-
-
Lodge, E.P.1
Heathcock, C.H.2
-
60
-
-
0344137670
-
-
Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2499-2506
-
-
Van Draanen, N.A.1
Arseniyadis, S.2
Crimmins, M.T.3
Heathcock, C.H.4
-
61
-
-
0001131963
-
-
For another example of the importance of dipole alignment in aldol TSs, see: Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 12368-12369
-
-
Boeckman Jr., R.K.1
Connell, B.T.2
-
62
-
-
0000784039
-
-
3,4 In fact, if a TS is drawn for aldol reactions with this aldehyde, a steric interaction of the aforementioned type will always be present for all rotamers around the tBu-CO bond.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4151-4157
-
-
Roush, W.R.1
-
63
-
-
0034814540
-
-
The various factors that may influence the stereochemical outcome of aldol reactions have been very lucidly analyzed by Danishefsky and co-workers in a recent publicaction: Lee, C. B.; Wu, Z.; Zhang, F.; Chappell, M. D.; Stachel, S. J.; Chou, T.-C.; Guan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 5249-5259.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5249-5259
-
-
Lee, C.B.1
Wu, Z.2
Zhang, F.3
Chappell, M.D.4
Stachel, S.J.5
Chou, T.-C.6
Guan, Y.7
Danishefsky, S.J.8
-
64
-
-
25444450504
-
-
note
-
This was established upon examination of NMR data for the crude aldol mixtures. In view of this synthetically useless result, we did not attempt to isolate individual compounds.
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-
-
-
65
-
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0033516716
-
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Provided that chelation is not involved in the transition state, achiral enolates react with α-oxygenated aldehydes to yield predominantly, albeit with variable diastereoselectivity, the Felkin aldols. See refs 1 and 2. For more recent cases, see, for example: (a) Esteve, C.; Ferrerò, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5079-5082.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5079-5082
-
-
Esteve, C.1
Ferrerò, M.2
Romea, P.3
Urpí, F.4
Vilarrasa, J.5
-
66
-
-
0033524878
-
-
(b) Lu, L.; Chang, H.-Y.; Fang, J.-M. J. Org. Chem. 1999, 64, 843-853.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 843-853
-
-
Lu, L.1
Chang, H.-Y.2
Fang, J.-M.3
-
67
-
-
0032568910
-
-
However, it is worth noting that Felkin aldols have been found to predominate in some reactions where chelation is likely to occur: Grandel, R.; Kazmaier, U.; Rominger, F. J. Org. Chem. 1998, 63, 4524-4528.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4524-4528
-
-
Grandel, R.1
Kazmaier, U.2
Rominger, F.3
-
68
-
-
0000763561
-
-
For nucleophilic additions to aldehydes bearing α-heteroatoms other than oxygen, see, for example: (a) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162 (α-amino aldehydes).
-
(1999)
Chem. Rev.
, vol.99
, pp. 1121-1162
-
-
Reetz, M.T.1
-
69
-
-
0030041646
-
-
(b) Enders, D.; Piva, O.; Burkamp, F. Tetrahedron 1996, 52, 2893-2908 (α-sulphenyl aldehydes).
-
(1996)
Tetrahedron
, vol.52
, pp. 2893-2908
-
-
Enders, D.1
Piva, O.2
Burkamp, F.3
-
70
-
-
0033809861
-
-
(c) Enders, D.; Adam, J.; Klein, D.; Otten, T. Synlett 2000, 1371-1384 (α-silyl aldehydes).
-
(2000)
Synlett
, pp. 1371-1384
-
-
Enders, D.1
Adam, J.2
Klein, D.3
Otten, T.4
-
73
-
-
15844390521
-
-
See also: Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
-
(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 7162-7166
-
-
Paddon-Row, M.N.1
Rondan, N.G.2
Houk, K.N.3
-
74
-
-
84989569853
-
-
Doubly diastereoselective aldol reactions of chiral enolates with chiral α-oxygenated aldehydes are not extensively documented in the literature. Matched and mismatched processes have been reported, with the full range from total stereocontrol by the enolate to complete dominance of the aldehyde being observed. See refs 1 and 2 and, for further cases: (a) Nicolaou, K. C.; Piscopio, A. D.; Bertinato, P.; Chakraborty, T. K.; Minowa, N.; Koide, K. Chem.-Eur. J. 1995, 1, 318-333.
-
(1995)
Chem.-Eur. J.
, vol.1
, pp. 318-333
-
-
Nicolaou, K.C.1
Piscopio, A.D.2
Bertinato, P.3
Chakraborty, T.K.4
Minowa, N.5
Koide, K.6
-
75
-
-
0030858177
-
-
(b) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 5864-5872
-
-
Sibi, M.P.1
Lu, J.2
Edwards, J.3
-
77
-
-
0033516536
-
-
(d) Esteve, C.; Ferrerò, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5083-5086.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5083-5086
-
-
Esteve, C.1
Ferrerò, M.2
Romea, P.3
Urpí, F.4
Vilarrasa, J.5
-
78
-
-
0035794851
-
-
(e) Nicolaou, K. C.; Pihko, P. M.; Diedrichs, N.; Zou, N.; Bernal, F. Angew. Chem., Int. Ed. 2001, 40, 1262-1265.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1262-1265
-
-
Nicolaou, K.C.1
Pihko, P.M.2
Diedrichs, N.3
Zou, N.4
Bernal, F.5
-
79
-
-
0035477181
-
-
(f) Forsyth, C. J.; Hao, J.; Aiguade, J. Angew. Chem., Int. Ed. 2001, 40, 3663-3667.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 3663-3667
-
-
Forsyth, C.J.1
Hao, J.2
Aiguade, J.3
-
80
-
-
10244241903
-
-
(g) Davies, S. G.; Nicholson, R. L.; Smith, A. D. Org. Biomol. Chem. 2004, 2, 3385-3400.
-
(2004)
Org. Biomol. Chem.
, vol.2
, pp. 3385-3400
-
-
Davies, S.G.1
Nicholson, R.L.2
Smith, A.D.3
-
81
-
-
0041344683
-
-
For a recent review on doubly and multiply stereoselective reactions, see: Kolodiazhnyi, O. I. Tetrahedron 2003, 59, 5953-6018.
-
(2003)
Tetrahedron
, vol.59
, pp. 5953-6018
-
-
Kolodiazhnyi, O.I.1
-
82
-
-
0028804044
-
-
Excluded from this discussion are chiral enolates in which the chirality resides in the ligands bound to the heteroatom. In these cases, stereocontrol by the chiral auxiliary is usually observed. See, for example: Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248-6249.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6248-6249
-
-
Gennari, C.1
Pain, G.2
Moresca, D.3
-
83
-
-
84988075033
-
-
(a) Bedorf, N.; Schomburg, D.; Gerth, K.; Reichenbach, H.; Höfle, G. Liebigs Ann. Chem. 1993, 1017-1021.
-
(1993)
Liebigs Ann. Chem.
, pp. 1017-1021
-
-
Bedorf, N.1
Schomburg, D.2
Gerth, K.3
Reichenbach, H.4
Höfle, G.5
-
84
-
-
0028154083
-
-
(b) Gerth, K.; Bedorf, N.; Irschik, H.; Höfle, G.; Reichenbach, H. J. Antibiot. 1994, 47, 23-31.
-
(1994)
J. Antibiot.
, vol.47
, pp. 23-31
-
-
Gerth, K.1
Bedorf, N.2
Irschik, H.3
Höfle, G.4
Reichenbach, H.5
-
85
-
-
0142164488
-
-
(c) Gerth, K.; Pradella, S.; Perlova, O.; Beyer, S.; Müller, S. J. Biotechnol. 2003, 106, 233-253.
-
(2003)
J. Biotechnol.
, vol.106
, pp. 233-253
-
-
Gerth, K.1
Pradella, S.2
Perlova, O.3
Beyer, S.4
Müller, S.5
-
86
-
-
0038379068
-
-
(a) Hill, A. M.; Thompson, B. L.; Harris, J. P.; Segret, R. Chem. Commun. 2003, 1358-1359.
-
(2003)
Chem. Commun.
, pp. 1358-1359
-
-
Hill, A.M.1
Thompson, B.L.2
Harris, J.P.3
Segret, R.4
-
88
-
-
0032940962
-
-
Abel, S.; Faber, D.; Hüter, O.; Giese, B. Synthesis 1999, 188-197.
-
(1999)
Synthesis
, pp. 188-197
-
-
Abel, S.1
Faber, D.2
Hüter, O.3
Giese, B.4
-
89
-
-
0028839668
-
-
(a) Loubinoux, B.; Sinnes, J.-L.; O'Sullivan, A. C.; Winkler, T. J. Org. Chem. 1995, 60, 953-959.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 953-959
-
-
Loubinoux, B.1
Sinnes, J.-L.2
O'Sullivan, A.C.3
Winkler, T.4
-
90
-
-
37049070911
-
-
(b) Loubinoux, B.; Sinnes, J.-L.; O'Sullivan, A. C. J. Chem. Soc., Perkin Trans. 1 1995, 521-525.
-
(1995)
J. Chem. Soc., Perkin Trans. 1
, pp. 521-525
-
-
Loubinoux, B.1
Sinnes, J.-L.2
O'Sullivan, A.C.3
-
91
-
-
0029149734
-
-
(c) Gurjar, M. K.; Mainkar, A. S.; Srinivas, P. Tetrahedron Lett. 1995, 36, 5967-5968.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 5967-5968
-
-
Gurjar, M.K.1
Mainkar, A.S.2
Srinivas, P.3
-
92
-
-
0037152307
-
-
(d) Cao, Y.; Eweas, A. F.; Donaldson, W. A. Tetrahedron Lett. 2002, 43, 7831-7834.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7831-7834
-
-
Cao, Y.1
Eweas, A.F.2
Donaldson, W.A.3
-
93
-
-
10644282962
-
-
(e) Park, S. H.; Lee, H. W.; Park, S.-U. Bull. Korean Chem. Soc. 2004, 25, 1613-1614.
-
(2004)
Bull. Korean Chem. Soc.
, vol.25
, pp. 1613-1614
-
-
Park, S.H.1
Lee, H.W.2
Park, S.-U.3
-
96
-
-
1842712344
-
-
See also: Bissen, M.; Mazur, R.; Quebbemann, H.-G.; Pennemann, K.-H. Helv. Chim. Acta 2004, 87, 524-535.
-
(2004)
Helv. Chim. Acta
, vol.87
, pp. 524-535
-
-
Bissen, M.1
Mazur, R.2
Quebbemann, H.-G.3
Pennemann, K.-H.4
-
97
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25444467086
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note
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In our first approach to 13, MOM protecting groups were used for the hydroxyl functions of diol 14. However, they proved incompatible with the acidic reaction conditions necessary for the deprotection of the cyclohexanone acetal: a great amount of decomposition was observed under a variety of conditions, as well as formation of formaldehyde acetals as byproducts.
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99
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0003405157
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Georg Thieme Verlag: Stuttgart
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(b) Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2004; pp 133-137. For instance, acidic conditions such as 80% aq AcOH or PPTS/MeOH gave yields of around 50-60% (based on recovered starting material), together with ill-defined byproducts.
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(2004)
Protecting Groups, 3rd Ed.
, pp. 133-137
-
-
Kocienski, P.J.1
-
101
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0003609963
-
-
Wiley: New York, Coll.
-
Meerwein, H. Organic Syntheses; Wiley: New York, 1973; Coll. Vol. V, pp 1096-1098.
-
(1973)
Organic Syntheses
, vol.5
, pp. 1096-1098
-
-
Meerwein, H.1
-
106
-
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0001091186
-
-
Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford
-
(b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2, pp 239-276. See also ref 2.
-
(1993)
Comprehensive Organic Synthesis
, vol.2
, pp. 239-276
-
-
Kim, B.M.1
Williams, S.F.2
Masamune, S.3
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107
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0025108083
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At least one case is known where the strong Felkin stereofacial bias of an α-oxygenated aldehyde forced the formation of an anti aldol from the Z-boron enolate of a chiral N-acyloxazolidinone: Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031. In the present case, however, a matched double diastereoselection can be expected between the known facial preference of the boron enolate of 21 and the Felkin bias of aldehyde 20: both factors predict here a predominant enolate attack to the aldehyde carbonyl Si face. For a very similar situation, see ref 29b.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 7001-7031
-
-
Evans, D.A.1
Kaldor, S.W.2
Jones, T.K.3
Clardy, J.4
Stout, T.J.5
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110
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note
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3 or Li di-tert-butyldiphenylide) are precluded here due to the presence of the α-alkoxy ketone moiety. We are presently investigating other methods to improve the yield of this critical deprotection step, as well as the use of alternative protecting groups.
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