Improved Methodology for the Preparation of Chiral Amines

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[36] E. W. Baxter, A. B. Reitz, Organic reactions; Wiley: New York, 2002; Vol. 59. [37] M. B. Smith, J. March, March’s advanced organic chemistry; Wiley: New York, 2001. [38] a) S. Bhattacharyya, Tetrahedron Lett. 1994, 35, 2401; b) S. Bhattacharyya, J. Org. Chem. 1995, 60, 4928; c) K. A. Neidigh, M. A. Avery, J. S. Williamson, S. Bhattacharyya, J. Chem. Soc., Perkin Trans. 1, 1998, 2527. [39] R. J. Mattson, K. M. Pham, D. J. Leuck, K. A. Cowen, J. Org. Chem. 1990, 55, 2552. [40] M. T. Reetz, Organotitanium reagents in organic synthesis; Springer-Verlag: Berlin, 1986; p 107. [41] a) B.T. Cho, S. K. Kang, Tetrahedron 2005, 61, 5725 ; b) S. Sato, T. Sakamoto, E. Miyazawa, Y. Kikugawa, Tetrahedron 2004, 60, 7899. [42] a) T. Suwa, E. Sugiyama, I. Shibata, A. Baba, Synthesis 2000, 789; b) T. Suwa, E. Sugiyama, I. Shibata, A. Baba, Synlett 2000, 556. [43] H. -U. Blaser, H. -P. Buser, H. -P. Jalett, B. Pugin, F. Spindler, Synlett 1999, 867. [44] Y. Chi, Y.-G. Zhou, X. Zhang, J. Org. Chem. 2003, 68, 4120. [45] L. R. Pérez, F. J. P.-Flores, P. Sharma, L. Velasco, A. Cabrera Org. Lett. 2009, 11, 265. [46] C. Li, B. V.-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967. [47] G. Borg, D. A. Cogan, J. A. Ellman, Tetrahedron Lett. 1999, 40, 6709. [48] J. Tanuwidjaja, H. M. Peltier, J. A. Ellman, J. Org. Chem. 2007, 72, 626. [49] G. Dutheuil, S. C. -Bonnaire, X. Pannecoucke, Angew. Chem. Int. Ed. 2007, 46, 1290. [50] A. Alexakis, S. Gille, F. Prian, S. Rosset, K. Ditrich, Tetrahedron Lett. 2004, 45, 1449. [51] T. C. Nugent, R. Seemeyer, WO2004035575, 2004. [52] a) T. C. Nugent, A. K. Ghosh, V. N. Wakchaure, R. R. Mohanty, Adv. Synth. Catal. 2006, 348, 1289; b) T. C. Nugent, Chiral Amine Synthesis - Strategies, Examples, and Limitations. In Process Chemistry in the Pharmaceutical Industry, Second Edition: Challenges in an Ever-Changing Climate, T. F. Braish, K. Gadamasetti Eds.; CRC Press- Taylor and Francis Group: New York, 2008; c) T. C. Nugent, A. K. Ghosh, V. N. Wakchaure, R. R. Mohanty, WO2006030017, 2006; d) T. C. Nugent, V. N. Wakchaure, A. K. Ghosh, R. R. Mohanty, Org. lett. 2005, 7, 4967; e) T. C. Nugent, A. K. Ghosh, Eur. J. Org. Chem. 2007, 3863. [53] R.Noyori, Adv. Synth. Catal. 2003, 345, 15 [54] M. Kitamura, D. Lee, S. Hayashi, S. Tanaka, M. Yoshimura, J. Org. Chem. 2002, 7, 8685 78
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Improved Methodology for the Prepar
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This dissertation is dedicated to a
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suppressing alcohol formation and p
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Prof. Mohamed El-Azizi, Prof. Abdel
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Et EtOH EtOAc GC h HPLC HRMS Hz J K
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Table of Contents Abstract. Acknowl
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4.1.5. Synthesis of Emitine 85 4.1.
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Chapter 1 Introduction 1.1. Chiral
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1. Cis-trans or geometric isomers.
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O O O * NH Thalidomide (R)-active a
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One enantiomer may be responsible f
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1.5.1. Synthesis of Enantiomericall
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1.5.2.2. Kinetic Resolution Kinetic
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compound by the auxiliary. The auxi
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1.5.4. Stereoselective Conversion o
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It is estimated that 3000 tonnes (a
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k R R P 1 k rac S k S P 2 Figure 1.
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(S)-(α)-Methylbenzylamine and its
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fourth chapter showing different dr
Page 39 and 40:
Burk was successful in reducing ary
Page 41 and 42: Table 1.1 Rhodium Catalyzed Reducti
Page 43 and 44: [8] E. L. Eliel, S. H. Wilen, Stere
Page 45 and 46: [42] a) J. Blacker, Innovations in
Page 47 and 48: [67] a) H. Qin, N. Yamagiwa, S. Mat
Page 49 and 50: of imine reduction in the past eigh
Page 51 and 52: 8 years beginning from the year 200
Page 53 and 54: 2.2.3. Nguyen Special Substrates. A
Page 55 and 56: Figure 2.4 General Catalyst structu
Page 57 and 58: 2.3.2. Different Substrates Categor
Page 59 and 60: H 2 , toluene, 25 °C, 4 h an ee of
Page 61 and 62: 1). They described the role of each
Page 63 and 64: More recently, 2008, he described t
Page 65 and 66: [22] E. Guiu, M. Aghmiz, Y. Diaz, C
Page 67 and 68: Chapter 3 Reductive Amination 3.1.
Page 69 and 70: . CH 3 CO(CH 2 ) 5 CH 3 H 2 NCH 2 C
Page 71 and 72: superior in terms of conversion (89
Page 73 and 74: O NHR 3 R 4 R 4 R 3 N OTi(O i Pr) 3
Page 75 and 76: Scheme 3.9. Synthesis of (S)-Metola
Page 77 and 78: groups decreased both the enantiose
Page 79 and 80: progress of the reaction was monito
Page 81 and 82: attempts were directed for the asym
Page 83 and 84: hydrogen bonding, is chiral and its
Page 85 and 86: Later he utilized this methodology
Page 87 and 88: OMe OMe O HN HN HN O 2 N 71 % yield
Page 89 and 90: compared to the oil refinery indust
Page 91: [14] V. I. Tararov, R. Kadyrov, T.H
Page 95 and 96: Chapter 4 Drugs and Reductive Amina
Page 97 and 98: Scheme 4.2. Synthesis of Muraglitaz
Page 99 and 100: Studies showed that the active isom
Page 101 and 102: aminoacid producing the protected a
Page 103 and 104: O NH 2 1. p-TsOH/toluene 2. BH 3 -T
Page 105 and 106: O O 125 NH 2 a 93% O O 126 H Bu N T
Page 107 and 108: ethyl carbamate by acylation with e
Page 109 and 110: 4.1.16. Synthesis of Ritonavir and
Page 111 and 112: 4.2. Conclusion Different important
Page 113 and 114: Chapter 5 Stoichiometric Use of Ytt
Page 115 and 116: The unique feature of this methodol
Page 117 and 118: Ytterbium triflate is the most comm
Page 119 and 120: Ruthenium(III) chloride 31.7 4 4.2
Page 121 and 122: t-Butyl methyl ether 15 - - 82 Hexa
Page 123 and 124: 2-octanone starting material. When
Page 125 and 126: 3 Yb(OTf) 3 d 4 Ti(O i Pr) 4 e 5 B(
Page 127 and 128: If a [1,3]-proton shift of the init
Page 129 and 130: enhanced stereoselectivity. For exa
Page 131 and 132: WO2006030017, 2006; c) T. C. Nugent
Page 133 and 134: 4 60 86 5 50 86 6 40 84 7 20 79 8 2
Page 135 and 136: The reactions described above all u
Page 137 and 138: e.g. compare entries 1, 5, 6, and 9
Page 139 and 140: solvent in the stoichiometric and c
Page 141 and 142: [2] Farina, V.; Grozinger, K.; Mül
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congested which should be favored.
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imine area % (GC analysis) time (mi
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Inversion at the nitrogen atom of t
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anti-6) would be expected to have m
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e.g. AcOH, suppresses alcohol by-pr
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eductive amination of a prochiral k
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Appendix Experimental Section Gener
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and the mixture was stirred for 30
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Reaction details: Yb(OAc) 3 (1.1 eq
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etention time [min]: major (S,S)-2b
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time [min]: major (S,S)-2c isomer,
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obtain the hydrochloride salt (0.41
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with etheral HCl provided the hydro
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Research experience: Date Project S
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