-
1
-
-
68249126331
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-
For selected reviews, see
-
For selected reviews, see:
-
-
-
-
7
-
-
68249132696
-
-
For examples of menthyl derived auxiliaries, see
-
For examples of menthyl derived auxiliaries, see:
-
-
-
-
9
-
-
0027295023
-
-
For examples of carbohydrate derived auxiliaries, see:
-
Drewes S.E., Emslie N.D., and Kahn A.A. Synth. Commun. 23 (1993) 1215 For examples of carbohydrate derived auxiliaries, see:
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Synth. Commun.
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Drewes, S.E.1
Emslie, N.D.2
Kahn, A.A.3
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10
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-
0035902414
-
-
For examples of pyrazolidinone derived auxiliaries, see:
-
Krishna R., Kannan V., Ilanogovan A., and Sharma G.V.M. Tetrahedron: Asymmetry 12 (2001) 829 For examples of pyrazolidinone derived auxiliaries, see:
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(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 829
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Krishna, R.1
Kannan, V.2
Ilanogovan, A.3
Sharma, G.V.M.4
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11
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0001260024
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For examples employing Oppolzer′s camphor sultam auxiliary, see:
-
Yang K.S., and Chen K. Org. Lett. 2 (2000) 729 For examples employing Oppolzer′s camphor sultam auxiliary, see:
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Org. Lett.
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Yang, K.S.1
Chen, K.2
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33
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0001362528
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Marino J.P., Viso A., Lee J.-D., de la Pradilla R.F., Fernandez P., and Rubio M.B. J. Org. Chem. 62 (1997) 645
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Marino, J.P.1
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de la Pradilla, R.F.4
Fernandez, P.5
Rubio, M.B.6
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Li G., Wei H.-X., Phelps B.S., Purkiss D.W., and Kim S.H. Org. Lett. 3 (2001) 823
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Org. Lett.
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Li, G.1
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Kim, S.H.5
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37
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34249988237
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Chernega A., Davies S.G., Elend D.L., Smethurst C.A.P., Roberts P.M., Smith A.D., and Smyth G.D. Tetrahedron 63 (2007) 7036
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Tetrahedron
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Chernega, A.1
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Elend, D.L.3
Smethurst, C.A.P.4
Roberts, P.M.5
Smith, A.D.6
Smyth, G.D.7
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39
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0034699412
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Bull S.D., Davies S.G., Key M.-S., Nicholson R.L., and Savory E.D. Chem. Commun. (2000) 1721
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(2000)
Chem. Commun.
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Bull, S.D.1
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Key, M.-S.3
Nicholson, R.L.4
Savory, E.D.5
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40
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33746191442
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Bull S.D., Davies S.G., Garner A.C., Kruchinin D., Key M.-S., Roberts P.M., Savory E.D., Smith A.D., and Thomson J.E. Org. Biomol. Chem. 4 (2006) 2945
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Bull, S.D.1
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Kruchinin, D.4
Key, M.-S.5
Roberts, P.M.6
Savory, E.D.7
Smith, A.D.8
Thomson, J.E.9
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41
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34248387352
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-
For a related example utilising the titanium enolate of an N-acyl SuperQuat, see:
-
For a related example utilising the titanium enolate of an N-acyl SuperQuat, see:. Sakaguchi H., Tokuyama H., and Fukuyama T. Org. Lett. 9 (2007) 1635
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(2007)
Org. Lett.
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Sakaguchi, H.1
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Trost B.M., and Fleming I. (Eds), Pergamon, New York, NY
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Heathcock C.H. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 133-238
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Heathcock, C.H.1
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43
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0001091186
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Trost B.M., and Fleming I. (Eds), Pergamon, New York, NY
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Kim B.M., Williams S.F., and Masamune S. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 239-275
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Comprehensive Organic Synthesis
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Kim, B.M.1
Williams, S.F.2
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44
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0001653533
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Trost B.M., and Fleming I. (Eds), Pergamon, New York, NY
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Paterson I. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 301-319
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Paterson, I.1
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47
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0347195435
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Heathcock C.H., Buse C.T., Kleschnick W.A., Pirrung M.C., Sohn J.E., and Lampe J. J. Org. Chem. 45 (1980) 1066
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Heathcock, C.H.1
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Pirrung, M.C.4
Sohn, J.E.5
Lampe, J.6
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49
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68249116941
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For examples of secondary lithium amides undergoing conjugate addition reactions to α,β-unsaturated N-acyl oxazolidinones, see
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For examples of secondary lithium amides undergoing conjugate addition reactions to α,β-unsaturated N-acyl oxazolidinones, see:
-
-
-
-
51
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34547869604
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Beddow J.E., Davies S.G., Ling K.B., Roberts P.M., Russell A.J., Smith A.D., and Thomson J.E. Org. Biomol. Chem. 5 (2007) 2812
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Beddow, J.E.1
Davies, S.G.2
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Smith, A.D.6
Thomson, J.E.7
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52
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0001266662
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Bull S.D., Davies S.G., Jones S., and Sanganee H.J. J. Chem. Soc., Perkin Trans. 1 (1999) 387
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J. Chem. Soc., Perkin Trans. 1
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Bull, S.D.1
Davies, S.G.2
Jones, S.3
Sanganee, H.J.4
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0001661322
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Alcock S.G., Baldwin J.E., Bohlmann R., Harwood L.M., and Seeman J.I. J. Org. Chem. 50 (1985) 3526
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Alcock, S.G.1
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Guha S.K., Shibayama A., Abe D., Ukaji Y., and Inomata K. Chem. Lett. 32 (2003) 778
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(2003)
Chem. Lett.
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Guha, S.K.1
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Guha S.K., Shibayama A., Abe D., Sakaguchi M., Ukaji Y., and Inomata K. Bull. Chem. Soc. Jpn. 77 (2004) 2147
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Inomata, K.6
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66
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68249089615
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note
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3N, THF, rt, 2 h; (ii) DBU, THF, rt, 2 h.
-
-
-
-
67
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-
68249111779
-
-
note
-
SuperQuat 11 was also isolated in 9% yield.
-
-
-
-
69
-
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68249110310
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-
note
-
Within the crystal lattice for compound 17 intermolecular hydrogen bonding is observed between the C(3′)-hydroxyl groups and the C(1′)-carbonyl groups.
-
-
-
-
73
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68249104553
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-
note
-
1H NMR coupling constant analysis with 51 and 52 displaying diagnostic coupling constants of 3.6 and 4.0 Hz, respectively between the C(2′)H and C(3′)H protons, indicative of a syn-configuration. Furthermore, recrystallisation of the minor diastereoisomeric product of the reaction with isobutyraldehyde allowed the syn-relative configuration of the minor aldol product 52 to be unambiguously determined by X-ray crystallographic analysis, with the absolute (4S,2′R,3′S)-configuration assigned relative to the known (S)-configuration of the C(4)-stereogenic centre. Within the crystal lattice for compound 52 intermolecular hydrogen bonding is observed between the C(3′)-hydroxyl groups and the C(1′)-carbonyl groups.{A figure is presented} Chem3D representation of the single crystal X-ray structure of 52 (some H atoms have been omitted for clarity).
-
-
-
-
74
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68249097907
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note
-
Within the crystal lattice for compound 22 intermolecular hydrogen bonding is observed between the C(3′)-hydroxyl groups and the C(2)-carbonyl groups, whereas for compound 23 intermolecular hydrogen bonding is observed between the C(3′)-hydroxyl groups and the C(1′)-carbonyl groups.
-
-
-
-
75
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68249123402
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note
-
No aldol products were isolated upon reaction with pivalaldehyde, presumably due to its steric bulk precluding reaction.
-
-
-
-
76
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68249116187
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-
note
-
In each case, β,γ-unsaturated 12 was isolated (typically in ∼20% yield), along with small amounts (<5%) of SuperQuat auxiliary 11.
-
-
-
-
77
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68249094800
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-
note
-
1H NMR spectrum of the crude reaction mixture and the pure product).
-
-
-
-
78
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68249085454
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For examples of base-catalysed processes, see
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For examples of base-catalysed processes, see:
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-
-
-
79
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68249103758
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Ruano G.J.L., Fernandez I., del Prado C.M., Hermoso J.A., Sanz-Aparicio J., and Martinez-Ripoll M. J. Org. Chem. 21 (1998) 7157
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Ruano, G.J.L.1
Fernandez, I.2
del Prado, C.M.3
Hermoso, J.A.4
Sanz-Aparicio, J.5
Martinez-Ripoll, M.6
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82
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68249113866
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For examples of acid-catalysed processes, see:
-
For examples of acid-catalysed processes, see:. Hayakawa S., Michiue T., Okamoto M., Hatakeyama S., and Ohta S. Heterocycles 2 (1998) 457
-
(1998)
Heterocycles
, vol.2
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Hayakawa, S.1
Michiue, T.2
Okamoto, M.3
Hatakeyama, S.4
Ohta, S.5
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83
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5244370033
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Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518
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(1996)
Organometallics
, vol.15
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Pangborn, A.B.1
Giardello, M.A.2
Grubbs, R.H.3
Rosen, R.K.4
Timmers, F.J.5
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84
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49149123176
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Department of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Oxford, UK
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Betteridge P.W., Carruthers J.R., Cooper R.I., Prout C.K., and Watkin D.J. Crystals (2001), Department of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Oxford, UK
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(2001)
Crystals
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Betteridge, P.W.1
Carruthers, J.R.2
Cooper, R.I.3
Prout, C.K.4
Watkin, D.J.5
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