8.28 Spectroscopic Analysis: NMR and Shift Reagents

Comprehensive Chirality

Volumn 8, Issue , 2012, Pages 545-570

  Wenzel, T J ^a  

^a BATES COLLEGE   (United States)

Author keywords

Absolute configuration; Chiral derivatizing agents; Chiral liquid crystals; Chiral metal complexes; Chiral solvating agents; Enantiomeric excess; Enantiomeric purity; NMR spectroscopy

Indexed keywords

EID: 84897004468     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-095167-6.00844-2     Document Type: Chapter

References (152)

1. Raban M., Mislow K. Tetrahedron Lett. 1965, 6:4249-4253.
2. Pirkle W.H. J. Am. Chem. Soc. 1966, 88:1837.
3. Hinckley C.C. J. Am. Chem. Soc. 1969, 91:5160-5162.
4. Whitesides G.M., Lewis D.W. J. Am. Chem. Soc. 1970, 92:6979-6980.
5. Sackmann E., Meiboom S., Snyder L.C. J. Am. Chem. Soc. 1968, 90:2183-2184.
6. Dale J.A., Mosher H.S. J. Am. Chem. Soc. 1973, 95:512-519.
7. Wenzel T.J. Discrimination of Chiral Compounds Using NMR Spectroscopy 2007, Wiley Interscience, Hoboken, NJ.
8. Seco J.M., Quinoa E., Riguera R. Chem. Rev. 2004, 104:17-117.
9. Wenzel T.J., Chisholm C.D. Chirality 2011, 23:190-214.
10. Wenzel T.J., Chisholm C.D. Prog. NMR Spectrosc. 2011, 59:1-63.
11. Botsi A., Perly B., Hadjoudis E. Perkin Trans. 2 1997, 26:89-94.
12. Dodziuk H., Sitkowski J., Stefaniak L., Jurczak J., Sybilska D. Chem. Commun. 1992, 28:207-208.
13. Dodziuk H., Ejchart A., Lukin O., Vysotsky M.O. J. Org. Chem. 1999, 64:1502-1507.
14. Uccello-Barretta G., Balzano F., Caporusso A.M., Iodice A., Salvadori P. J. Org. Chem. 1995, 60:2227-2231.
15. Wenzel T.J., Amoono E.P., Shariff S.S., Aniagyei S.E. Tetrahedron: Asymmetry 2003, 14:3099-3104.
16. Dignam C.F., Randall L.A., Blacken R.D. Tetrahedron: Asymmetry 2006, 17:1199-1208.
17. Provencher K.A., Wenzel T.J. Tetrahedron: Asymmetry 2008, 19:1797-1803.
18. Owens P.K., Fell A.F., Coleman M.W., Berridge J.C. J. Inclusion Phenom. Macrocyclic Chem. 2000, 38:133-151.
19. Chisholm C.D., Wenzel T.J. Tetrahedron: Asymmetry 2011, 22:62-68.
20. Wenzel T.J., Thurston J.E. J. Org. Chem. 2000, 65:1243-1248.
21. Wenzel T.J., Freeman B.E., Sek D.C., et al. Anal. Bioanal. Chem. 2004, 378:1536-1547.
22. Wenzel T.J., Thurston J.E. Tetrahedron Lett. 2000, 41:3769-3772.
23. Machida Y., Kagawa M., Nishi H. J. Pharm. Biomed. Anal. 2003, 30:1929-1942.
24. Wenzel T.J., Bourne C.E., Clark R.L. Tetrahedron: Asymmetry 2009, 20:2052-2060.
25. Chisholm C.D., Fülöp F., Forró E., Wenzel T.J. Tetrahedron: Asymmetry 2010, 21:2289-2294.
26. Lovely A.E., Wenzel T.J. Org. Lett. 2006, 8:2823-2826.
27. Lovely A.E., Wenzel T.J. Tetrahedron: Asymmetry 2006, 17:2642-2648.
28. Lovely A.E., Wenzel T.J. J. Org. Chem. 2006, 71:9178-9182.
29. Lovely A.E., Wenzel T.J. Chirality 2008, 20:370-378.
30. Gutsche C.D. Calixarenes 1989, Royal Society of Chemistry, Cambridge, UK.
31. Yanagihara R., Tominaga M., Aoyama Y. J. Org. Chem. 1994, 59:6865-6867.
32. Dignam C.F., Zopf J.J., Richards C.J., Wenzel T.J. J. Org. Chem. 2005, 70:8071-8078.
33. Hagan K.A., O'Farrell C.M., Wenzel T.J. Eur. J. Org. Chem. 2009, 2009:4825-4832.
34. O'Farrell C.M., Chudomel J.M., Collins J.M., Dignam C.F., Wenzel T.J. J. Org. Chem. 2008, 73:2843-2851.
35. Pham N.H., Wenzel T.J. J. Org. Chem. 2011, 76:986-989.
36. Pirkle W.H., Beare S.D., Muntz R.L. Tetrahedron Lett. 1974, 15:2295-2298.
37. Buddrus J., Herzog H., Risch K. Anal. Chem. 1994, 66:40-42.
38. Pirkle W.H., Beare S.D. J. Am. Chem. Soc. 1967, 89:5485-5487.
39. Guette J.P., Lacombe L., Horeau A.C.R. Seances Acad. Sci. C 1968, 267:166-169.
40. MikoŁajczyk M., Omelanczuk J., Leitloff M., et al. J. Am. Chem. Soc. 1978, 100:7003-7008.
41. Glowacki Z., Hoffman M., Rachon J. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 82:39-47.
42. Mamlok L., Marquet A., Lacombe L. Tetrahedron Lett. 1971, 12:1039-1042.
43. Fidanze S., Song F., Szlosek-Pinaud M., Small P.L.C., Kishi Y. J. Am. Chem. Soc. 2001, 123:10117-10118.
44. Higashibayashi S., Kishi Y. Tetrahedron 2004, 60:11977-11982.
45. Kobayashi Y., Hayashi N., Kishi Y. Tetrahedron Lett. 2003, 44:7489-7491.
46. Uccello-Barretta G., Bardoni S., Balzano F., Salvadori P. Tetrahedron: Asymmetry 2001, 12:2019-2023.
47. Shapiro M.J., Archinal A.E., Jarema M.A. J. Org. Chem. 1989, 54:5826-5828.
48. Lacour J., Hebbe-Viton V. Chem. Soc. Rev. 2003, 32:373-382.
49. Lacour J., Moraleda D. Chem. Commun. 2009, 45:7073-7089.
50. Michon C., Goncalves-Farbos M.H., Lacour J. Chirality 2009, 21:809-817.
51. Deshmukh M., Dunach E., Juge S., Kagan H.B. Tetrahedron Lett. 1984, 25:3467-3470.
52. Dunach E., Kagan H.B. Tetrahedron Lett. 1985, 26:2649-2652.
53. Jursic B.S., Zdravkovski Z., Zuanic M. Tetrahedron: Asymmetry 1994, 5:1711-1716.
54. Iwaniuk D.P., Wolf C. J. Org. Chem. 2010, 75:6724-6727.
55. Pirkle W.H., Tsipouras A. Tetrahedron Lett. 1985, 26:2989-2992.
56. Koscho M.E., Pirkle W.H. Tetrahedron: Asymmetry 2005, 16:3345-3351.
57. Wenzel T.J., Miles R.D., Weinstein S.E. Chirality 1997, 9:1-9.
58. Wenzel T.J., Morin C.A., Brechting A.A. J. Org. Chem. 1992, 57:3594-3599.
59. Pirkle W.H., Sikkenga D.L. J. Org. Chem. 1975, 40:3430-3434.
60. Moon L.S., Pal M., Kasetti Y., Vharatam P.V., Jolly R.S. J. Org. Chem. 2010, 75:5487-5498.
61. Goering H.L., Eikenberry J.N., Koermer G.S. J. Am. Chem. Soc. 1971, 93:5913-5914.
62. Fraser R.R., Petit M.A., Saunders J.K. Chem. Commun. 1971, 7:1450-1451.
63. McCreary M.D., Lewis D.W., Wernick D.L., Whitesides G.M. J. Am. Chem. Soc. 1974, 96:1038-1054.
64. Wenzel T.J. NMR Shift Reagents 1978, CRC Press, Boca Raton, FL.
65. Ghosh I., Zeng H., Kishi Y. Org. Lett. 2004, 6:4715-4718.
66. Omata K., Aoyagi S., Kabuto K. Tetrahedron: Asymmetry 2004, 15:2351-2356.
67. Wenzel T.J., Bogyo M.S., Lebeau E.L. J. Am. Chem. Soc. 1994, 116:4858-4865.
68. Sweeting L.M., Crans D.C., Whitesides G.M. J. Org. Chem. 1987, 52:2273-2276.
69. Wenzel T.J., Wenzel B.T. Chirality 2009, 21:6-10.
70. Guo G., Persons J., Harbison G.S. Magn. Reson. Chem. 2006, 44:832-837.
71. Wenzel T.J., Sievers R.E. J. Am. Chem. Soc. 1982, 104:382-388.
72. Offermann W., Mannschreck A. Tetrahedron Lett. 1981, 22:3227-3230.
73. Kabuto K., Sasaki Y. Chem. Commun. 1987, 23:670-671.
74. Hazama R., Umakoshi K., Kabuto C., Kabuto K., Sasaki Y. Chem. Commun. 1996, 32:15-16.
75. Kabuto K., Sasaki Y. Tetrahedron Lett. 1990, 31:1031-1034.
76. Sasaki M., Omata K., Kabuto K., Sasaki Y. Kidorui 2003, 42:198-199.
77. Ogasawara K., Omata K., Kabuto K., Jin H., Sasaki Y. Kidorui 1999, 34:152-153.
78. Inamoto A., Ogasawara K., Omata K., Kabuto K., Sasaki Y. Org. Lett. 2000, 2:3543-3545.
79. Sato J., Jin H., Omata K., Kabuto K., Sasaki Y. Enantiomer 1999, 4:147-150.
80. Wild S.B. Coord. Chem. Rev. 1997, 166:291-311.
81. Dunina V.V., Kuz'mina L.G., Kazakova M.Y., et al. Tetrahedron: Asymmetry 1997, 8:2537-2545.
82. Parker D., Taylor R.J. Tetrahedron 1988, 44:2241-2248.
83. Cucciolito M.E., Flores G., Vitagliano A. Organometallics 2004, 23:15-17.
84. Uccello-Barretta G., Bernardini R., Balzano F., Salvadori P. Chirality 2002, 14:484-489.
85. Duddeck H. Chem. Record 2005, 5:1-14.
86. Mattiza J.T., Harada N., Kuwahara S., Hassan Z., Duddeck H. Chirality 2009, 21:843-849.
87. Farjon J., Ziani L., Beguin L., Merlet D., Courtieu J. Annu. Rep. NMR Spectrosc. 2007, 61:283-293.
88. Baishya B., Prabhu U.R., Suryaprakash N. Annu. Rep. NMR Spectrosc. 2009, 67:331-423.
89. Sarfati M., Lesot P., Merlet D., Courtieu J. Chem. Commun. 2000, 36:2069-2081.
90. Sarfati M., Aroulanda C., Courtieu J., Lesot P. Tetrahedron: Asymmetry 2001, 12:737-744.
91. Canet I., Courtieu J., Loewenstein A., Meddour A., Pechine J.M. J. Am. Chem. Soc. 1995, 117:6520-6526.
92. Ziani L., Lesot P., Meddour A., Courtieu J. Chem. Commun. 2007, 43:4737-4739.
93. Serhan Z., Martel L., Billault I., Lesot P. Chem. Commun. 2010, 46:6599-6601.
94. Thiele C.M. J. Org. Chem. 2004, 69:7403-7413.
95. Arnold L., Marx A., Thiele C.M., Reggelin M. Chem. Eur. J. 2010, 16:10342-10346.
96. Luy B. J. Indian Inst. Sci. 2010, 90:119-132.
97. Kummerlowe G., Luy B. Annu. Reports NMR Spectrosc. 2009, 68:193-230.
98. Kusumi T., Ohtani I.I. Biology-Chemistry Interface 1999, 103-137. Dekker, New York.
99. Louzao I., Seco J.M., Quinoa E., Riguera R. Chem. Commun. 2010, 46:7903-7905.
100. Harada N. Chirality 2008, 20:691-723.
101. Garcia R., Seco J.M., Vazquez S.A., Quinoa E., Riguera R. J. Org. Chem. 2002, 67:4579-4589.
102. Latypov S.K., Seco J.M., Quinoa E., Riguera R. J. Org. Chem. 1996, 61:8569-8577.
103. Omata K., Kotani K., Kabuto K., Fujiwara T., Takeuchi Y. Chem. Commun. 2010, 46:3610-3612.
104. Freire F., Seco J.M., Quinoa E., Riguera R. Chem. Commun. 2007, 43:1456-1458.
105. Takahashi H., Kato N., Iwashima M., Iguchi K. Chem. Lett. 1999, 28:1181-1182.
106. Seco J.M., Quinoa E., Riguera R. J. Org. Chem. 1999, 64:4669-4675.
107. Latypov S.K., Seco J.M., Quinoa E., Riguera R. J. Org. Chem. 1995, 60:1538-1545.
108. Hoye T.R., Renner M.K. J. Org. Chem. 1996, 61:8489-8495.
109. Porto S., Seco J.M., Ortiz A., Quinoa E., Riguera R. Org. Lett. 2007, 9:5015-5018.
110. Freire F., Seco J.M., Quinoa E., Riguera R. J. Org. Chem. 2005, 70:3778-3790.
111. Freire F., Seco J.M., Quinoa E., Riguera R. Org. Lett. 2005, 7:4855-4858.
112. Freire F., Seco J.M., Quinoa E., Riguera R. Org. Lett. 2010, 12:208-211.
113. Freire F., Lallana E., Quinoa E., Riguera R. Chem. Eur. J. 2009, 15:11963-11975.
114. Leiro V., Seco J.M., Quinoa E., Riguera R. Org. Lett. 2008, 10:2733-2736.
115. Kusumi T., Ooi T., Ohkubo Y., Yabuuchi T. Bull. Chem. Soc. Jpn. 2006, 79:965-980.
116. Ohtaki T., Akasaka K., Kabuto C., Ohrui H. Chirality 2005, 17:S171-S176.
117. Ravn M.M., Jin Q., Coates R.M. Eur. J. Org. Chem. 2000, 2000:1401-1410.
118. Parker D., Taylor R.J., Ferguson G., Tonge A. Tetrahedron 1986, 42:617-622.
119. Hamersak Z., Selestrin A., Lesac A., Sunjic V. Tetrahedron: Asymmetry 1998, 9:1891-1897.
120. Halpin R.A., El-Naggar S.F., McCombe K.M., et al. Tetrahedron Lett. 1982, 23:1655-1658.
121. Shim Y.J., Choi K. Org. Lett. 2010, 12:880-882.
122. Yabuuchi T., Kusumi T. J. Org. Chem. 2000, 65:397-404.
123. Hoye T.R., Koltun D.O. J. Am. Chem. Soc. 1998, 120:4638-4643.
124. Hoye T.R., Hamad A.S., Koltun D.O., Tennakoon M.A. Tetrahedron Lett. 2000, 41:2289-2293.
125. Suarez-Castillo O.R., Melendez-Rodriguez M., Castelan-Duarte L.E., et al. Tetrahedron: Asymmetry 2009, 20:2374-2389.
126. Alexakis A., Frutos J.C., Mangeney P. Tetrahedron: Asymmetry 1993, 4:2431-2434.
127. Noe C.R., Knollmüller M., Göstl G., Oberhauser B., Völlenkle H. Angew. Chem. Int. Ed. Engl. 1987, 26:442-444.
128. Akasaka K., Imaizumi K., Shichijyukari S., Ohrui H., Kabuto C. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1998, 40:79-84.
129. Ferreiro M.J., Latypov S.K., Quinoa E., Riguera R. J. Org. Chem. 2000, 65:2658-2666.
130. Berti F., Felluga F., Forzato C., et al. Tetrahedron: Asymmetry 2006, 17:2344-2353.
131. Brown J.M., Parker D. Organometallics 1982, 1:950-956.
132. Rawlings B.J., Reese P.B., Ramer S.E., Vederas J.C. J. Am. Chem. Soc. 1989, 111:3382-3390.
133. Hiemstra H., Wynberg H. Tetrahedron Lett. 1977, 18:2183-2186.
134. Lemiere G.L., Dommisse R.A., Lepoivre J.A., et al. J. Am. Chem. Soc. 1987, 109:1363-1370.
135. Buchwald S.L., Knowles J.R. J. Am. Chem. Soc. 1980, 102:6601-6602.
136. Arnold J.R.P., Lowe G. Chem. Commun. 1986, 22:865-867.
137. Hulst R., Kellogg R.M., Feringa B.L. Recl. Trav. Chim. Pays-Bas 1995, 114:115-138.
138. Murai T., Tsuji H., Imaizumi S., Maruyama T. Chem. Lett. 2010, 39:524-526.
139. Bredikhin A.A., Strunskaya E.I., Novikova V.G., et al. Russ. Chem. Bull. 2004, 53:213-218.
140. Wu R., Barr M.E., Hernandez G., Orji C.C., Silks L.A. Recent Res. Devel. Org. Bioorg. Chem. 1998, 2:29-42.
141. Wu R., Odom J.D., Dunlap R.B., Silks L.A. Tetrahedron: Asymmetry 1999, 10:1465-1470.
142. Kelly A.M., Perez-Fuertes T., Fossey J.S., et al. Nat. Protocols 2008, 3:215-219.
143. Kelly A.M., Bull S.D., James T.D. Tetrahedron: Asymmetry 2008, 19:489-494.
144. Perez-Fuertes Y., Kelly A.M., Fossey J.S., et al. Nat. Protocols 2008, 3:210-214.
145. Burgess K., Porte A.M. Angew. Chem. Int. Ed. Engl. 1994, 33:1182-1184.
146. Resnick S.M., Torok D.S., Gibson D.T. J. Org. Chem. 1995, 60:3546-3549.
147. Garcia-Martinez C., Taguchi Y., Oishi A., Hayamizu K. Tetrahedron: Asymmetry 1998, 9:955-965.
148. Fukui H., Fukushi Y., Tahara S. Tetrahedron Lett. 1999, 40:325-328.
149. Kobayashi Y., Tan C., Kishi Y. J. Am. Chem. Soc. 2001, 123:2076-2078.
150. Fleury E., Lannou M.I., Bistri O., et al. Eur. J. Org. Chem. 2009, 2009:4992-5001.
151. Seike H., Ghosh I., Kishi Y. Org. Lett. 2006, 8:3861-3864.
152. Schmidt Y., Breit B. Org. Lett. 2010, 12:2218-2221.