Recent advances in heterolytic nucleofugal leaving groups

Tetrahedron

Volumn 63, Issue 24, 2007, Pages 5103-5122

  Lepore, Salvatore D ^a   Mondal, Deboprosad ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

Activation deactivation leaving groups; Chiral leaving groups; Heterolytic leaving groups; NALG; New leaving groups; Nucleofugal; Nucleophile assisting leaving groups

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; 3,5 DICHLOROPYRIDINE; 4 PHENYL 1,2 DIHYDROXYQUINOLINE; ALKYL SULFONYL DERIVATIVE; AMINE; BENZENEDISULFONYLIMIDE DERIVATIVE; BENZOISOTHIAZOLE 3 ONE DERIVATIVE; BISMUTH DERIVATIVE; CARBORANE DERIVATIVE; CARBOXYLIC ACID; FLUOROCARBOXYLIC ACID; HETEROCYCLIC COMPOUND; IMIDAZOLE 1 SULFONIC ACID; INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PENTAFLUOROPHENYL; PYRIDINE SULFONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLINE SULFONIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE; TRIARYLBISMUTH; UNCLASSIFIED DRUG; VINYLOGOUS CARBONIC ACID DERIVATIVE; VINYLOGOUS CARBOXYLIC ACID DERIVATIVE; VINYLOGOUS SULFONIC ACID DERIVATIVE;

ALKYLATION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; NUCLEOLUS; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

EID: 34248198488     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.049     Document Type: Review

References (134)

1. Smith M.B., and March J. Advanced Organic Chemistry. 5th ed. (2001), John Wiley, New York, NY p 275
2. Muller P. Pure Appl. Chem. 66 (1994) 1077-1184
3. Mathieu J., Allais A., and Valls J. Angew. Chem. 72 (1960) 71-74
4. Based on a CAS database search using SciFinder Scholar 2006 searching the term 'leaving group' with the two words closely associated.
5. Bordwell F.G., Pitt B.M., and Knell M. J. Am. Chem. Soc. 73 (1951) 5004
6. Winstein S., Morse B.K., Grunwald E., Jones H.W., Corse J., Trifan D., and Marshall H. J. Am. Chem. Soc. 74 (1952) 1127-1132
7. Swain C.G., and Dittmer D.C. J. Am. Chem. Soc. 75 (1953) 4627
8. Lewis E.S., and Boozer C.E. J. Am. Chem. Soc. 76 (1954) 791-793
9. Including the popular undergraduate text by. Morrison R.T., and Boyd R.N. Organic Chemistry. 2nd ed. (1966), Allyn and Bacon, Boston, MA
10. Laue T., and Plagens A. Named Organic Reactions. 2nd ed. (2005), John Wiley, New York, NY p IX
11. Netscher T. Recent Res. Dev. Org. Chem. 7 (2003) 71-83
12. Katritzky A.R. Tetrahedron 36 (1980) 679-699
13. Katritzky A.R., and Musumarra G. Chem. Soc. Rev. (1984) 4768
14. Lou B., Eckhardt E., and Hanessian S. Preparative Carbohydrate Chemistry (1997), Dekker, New York, NY pp 449-466
15. Capozzi M.A.M., Cardellicchio C., and Naso F. Eur. J. Org. Chem. (2004) 1855-1863
16. For a recent comprehensive review, see:. Montalbetti C.A.G.N., and Falque V. Tetrahedron 61 (2005) 10827-10852
17. For a recent comprehensive review, see:. Dolle R.E. J. Comb. Chem. 7 (2005) 739-798
18. For representative examples:
19. Bulluss G.H., Knott K.M., Ma E.S.F., Aris S.M., Alvarado E., and Farrell N. Inorg. Chem. 45 (2006) 5733-5735
20. Parsons S., Smith A.A., and Winpenny R.E.P. Chem. Commun. (2000) 579-580
21. Pasini A., D'Alfonso G., Manzotti C., Moret M., Spinelli S., and Valsecchi M. Inorg. Chem. 33 (1994) 4140-4148
22. For representative examples:
23. Wood T.C., Johnson K.L., Naylor S., and Weinshilboum R.M. Drug Metab. Dispos. 30 (2002) 1123-1128
24. Hlasta D.J., Ackerman J.H., Court J.J., Farrell R.P., Johnson J.A., Kofron J.L., Robinson D.T., Talomie T.G., Dunlap R.P., and Franke C.A. J. Med. Chem. 38 (1995) 4687-4692
25. Krantz A., Copp L.J., Coles P.J., Smith R.A., and Heard S.B. Biochemistry 30 (1991) 4678-4687
26. Crossland R.K., Wells W.E., and Shiner V.J. J. Am. Chem. Soc. 93 (1971) 4217-4219
27. Farcasiu D., Jaehme J., and Ruechardt C. J. Am. Chem. Soc. 107 (1985) 5717-5722
28. Sorbye K., Tautermann C., Carlsen P., and Fiksdahl A. Tetrahedron: Asymmetry 9 (1998) 681-689
29. Heggvik L., and Fiksdahl A. Tetrahedron: Asymmetry 8 (1997) 2189-2192
30. Said S.A., and Fiksdahl A. Tetrahedron: Asymmetry 10 (1999) 2627-2633
31. Evans P.A., Brand T.A., and Robinson J.E. Tetrahedron Lett. 40 (1999) 3105-3108
32. Evans P.A., and Brandt T.A. Org. Lett. 1 (1999) 1563-1565
33. Liu J., and Robins M.J. Org. Lett. 7 (2005) 1149-1151
34. Vatele J., and Hanessian S. Preparative Carbohydrate Chemistry (1997), Dekker, New York, NY pp 127-149
35. Hanessian S., and Vatele J.M. Tetrahedron Lett. 22 (1981) 3579-3582
36. Vatele J.M., and Hanessian S. Tetrahedron 52 (1996) 10557-10568
37. Hanessian S., Bacquet C., and LeHong N. Carbohydr. Res. 80 (1980) C17
38. Hanessian S. Preparative Carbohydrate Chemistry (1997) pp 381-388
39. David S., Malleron A., and Dini C. Carbohydr. Res. 188 (1989) 193-200
40. Best W.M., MacDonald J.M., Skelton B.W., Stick R.V., Tilbrook D.M.G., and White A.H. Can. J. Chem. 80 (2002) 857-865
41. Attolino E., Catelani G., and D'Andrea F. Tetrahedron Lett. 43 (2002) 1685-1688
42. Corey E.J., Posner G.H., Atkinson R.F., Wingard A.K., Halloran D.J., Radzik D.M., and Nash J.J. J. Org. Chem. 54 (1989) 389-393
43. Paleta O., Pomeisl K., Kafka S., Klasek A., and Kubelka V. Beilstein J. Org. Chem. 1 (2005) 17
44. Imagawa H., Kinoshita A., Fukuyama T., Yamamoto H., and Nishizawa M. Tetrahedron Lett. 47 (2006) 4729-4731
45. Osa Y., Takeda K., Sato T., Kaji E., Mizuno Y., and Takayanagi H. Tetrahedron Lett. 40 (1999) 1531-1534
46. Mackie R.K., Smith D.M., and Aitken R.A. Guidebook to Organic Synthesis. 3rd ed. (1999), Longman, UK 302-303
47. Seyden-Penen J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis (1995), John Wiley, New York, NY
48. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 3 (1999), Springer, New York, NY
49. Bringmann G., Mortimer A.J.P., Keller P.A., Gresser M.J., Garner J., and Breuning M. Angew. Chem., Int. Ed. 44 (2005) 5384-5427
50. Wallace T.W. Org. Biomol. Chem. 4 (2006) 3197-3210
51. Nakamura H., Ishihara K., and Yamamoto H. J. Org. Chem. 67 (2002) 5124-5137
52. Ishihara K., Ishibashi H., and Yamamoto H. J. Am. Chem. Soc. 123 (2001) 1505-1506 and references cited therein
53. Fujii M., Sato Y., Aida T., and Yoshihara M. Chem. Express 7 (1992) 309
54. Murata S., Suzuki M., and Noyori R. J. Am. Chem. Soc. 102 (1980) 3248-3249
55. Sakane S., Fujiwara J., Maruoka K., and Yamamoto H. J. Am. Chem. Soc. 105 (1983) 6154-6155
56. Tamura R., Watabe K., Ono N., and Yamamoto Y. J. Org. Chem. 57 (1992) 4895-4903
57. Tamura R., Katayama H., Watabe K., and Suzuki H. Tetrahedron 46 (1990) 7557-7568
58. The use of chiral leaving groups in nitro-olefination reactions has been briefly reviewed:. Berner O.M., Tedeschi L., and Enders D. Eur. J. Org. Chem. 12 (2002) 1877-1894
59. Rajappa S. Tetrahedron 55 (1999) 7065-7114
60. Faulques M., Rene L., and Royer R. Synthesis 4 (1982) 260-261
61. Yang X., and Wand R. Tetrahedron: Asymmetry 8 (1997) 3275-3281
62. Fugi K., Node M., Nagasawa H., Naniwa Y., and Terada S. J. Am. Chem. Soc. 8 (1986) 3855-3856
63. Forzato C., Nitti P., Pitacco G., Valentin E., Morganti S., Rizzato E., Spinelli D., Dell'Erba C., Petrillo G., and Tavani C. Tetrahedron 60 (2004) 11011-11027
64. Fuji K. ACGC Chem. Res. Commun. 11 (2000) 32-37
65. Bagul T.D., Lakshmaiah G., Kawabata T., and Fuji K. Org. Lett. 4 (2002) 249-251
66. Basavaiah D., Kumaragurubaran N., Sharada D.S., and Reddy R.M. Tetrahedron 57 (2001) 8167-8172
67. Duhamel P., Valnot J.Y., and Eddine J.J. Tetrahedron Lett. 23 (1982) 2863-2866
68. Duhamel P., Ple G., and Valnot J.Y. Heterocycles 37 (1994) 751-757
69. McManus S.P., Roberts F.E., Lam D.H., and Hovanes B. J. Org. Chem. 47 (1982) 4386-4388
70. McManus S.P., Safavy K.K., and Roberts F.E. J. Org. Chem. 47 (1982) 4388-4389
71. Alexakis A., Malan C., Lea L., Tissot-Croset K., Polet D., and Falciola C. Chimia 60 (2006) 124-130
72. Karlström A.S.E., and Bäckvall J.-E. Copper-Mediated Enantioselective Substitution Reactions. In: Krause N. (Ed). Modern Organocopper Chemistry (2002), Wiley-VCH 262-269
73. Breit B., and Breuninger D. Synthesis (2005) 147-157
74. Breit B., and Breuninger D. Synthesis (2005) 2782-2786
75. Breit B., and Breuninger D. J. Am. Chem. Soc. 126 (2004) 10244-10245
76. Karlström A.S.E., Huerta F.F., Meuzelaar G.J., and Bäckvall J.-E. Synlett (2001) 923-926
77. Okuyama T., Takino T., Sueda T., and Ochiai M. J. Am. Chem. Soc. 117 (1995) 3360-3367
78. Ochiai M. J. Organomet. Chem. 611 (2000) 494-508
79. Stang P.J. J. Org. Chem. 68 (2003) 2997-3008
80. Matano Y. Organometallics 19 (2000) 2258-2263
81. Matano Y., and Imahori H. J. Org. Chem. 69 (2004) 5505-5508
82. Ooi T., Goto R., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 10494-10495
83. Koech P.K., and Krische M.J. J. Am. Chem. Soc. 126 (2004) 5350-5351
84. Moloney M.G., and Pinhey J.T. J. Chem. Soc., Chem. Commun. (1984) 965-966
85. Kato T., Stoyanov E., Geier J., Grutzmacher H., and Reed C.A. J. Am. Chem. Soc. 126 (2004) 12451-12457
86. Shimizu M., Sugano Y., Konakahara T., Gama Y., and Shibuya I. Tetrahedron 58 (2002) 3779-3783
87. Bao M., Shimizu M., Shimada S., Inoue J., and Konakahara T. Tetrahedron 60 (2004) 11359-11366
88. Al Neirabeyeh M., and Rollin P. J. Carbohydr. Chem. 9 (1990) 471-478
89. Wang J.C., and Just G. Tetrahedron Lett. 38 (1997) 2241-2244
90. Lesnikowski Z.J., Jaworska M., and Stec W.J. Tetrahedron Lett. 28 (1987) 5535-5538
91. Picci N., Pocci M., Gugliuzza A., Puoci F., De Munno A., Iemma F., and Bertini V. Heterocycles 55 (2001) 2075-2084
92. Arseniyadis S., Wagner A., and Mioskowski C. Tetrahedron Lett. 45 (2004) 2251-2253
93. See Ref. 16;
94. Fraser H.L., Floyd M.B., and Sosa A.C.B. Prog. Heterocycl. Chem. 17 (2005) 261-303
95. Wietzerbin K., Bernadou J., and Meunier B. Eur. J. Inorg. Chem. (2000) 1391-1406
96. Benkeser R.A., Siklosi M.P., and Mozdzen E.C. J. Am. Chem. Soc. 100 (1978) 2134-2139
97. Lomas J.S., and Dubois J.E. J. Org. Chem. 49 (1984) 2067-2069
98. Arnett E.M., Small L.E., McLver R.T., and Miller J.S. J. Org. Chem. 43 (1978) 815-817
99. Zook H.D., March J., and Smith D.F. J. Am. Chem. Soc. 81 (1959) 1617-1620
100. Garner C.M., and Fischer H.C. Tetrahedron Lett. 47 (2006) 7405-7407
101. Codee J.D.C., Litjens R.E.J.N., Van den Bos L.J., Overkleeft H.S., and Van der Marel G.A. Chem. Soc. Rev. 34 (2005) 769-782
102. Hanessian S., and Lou B. Chem. Rev. 100 (2000) 4443-4463
103. Pornsuriyasak P., Gangadharmath U.B., Rath N.P., and Demchenko A.V. Org. Lett. 6 (2004) 4515-4518
104. Mootoo D.R., Konradsson P., Udodong U.E., and Fraser-Reid B. J. Am. Chem. Soc. 110 (1988) 5583-5585
105. Demchenko A.V., Malysheva N.N., and De Meo C.D. Org. Lett. 5 (2003) 455-458
106. Kamat M.N., and Demchenko A.V. Org. Lett. 7 (2005) 3215-3218
107. Euzen R., Ferrieres V., and Plusquellec D. J. Org. Chem. 70 (2005) 847-855
108. Demchenko A.V., Pornsuriyasak P., De Meo C., and Malysheva N.N. Angew. Chem., Int. Ed. 43 (2004) 3069-3072
109. Pornsuriyasak P., and Demchenko A.V. Chem.-Eur. J. 12 (2006) 6630-6646
110. Pornsuriyasak P., and Demchenko A.V. Tetrahedron: Asymmetry 16 (2005) 433-439
111. De Meo C., and Parker O. Tetrahedron: Asymmetry 16 (2005) 303-307
112. Cacciapaglia R., Van Doorn A.R., Mandolini L., Reinhoudt D.N., and Verboom W. J. Am. Chem. Soc. 114 (1992) 2611-2617
113. Lu T., Yoo H.K., Zhang H., Bott S., Atwood J.L., Echegoyen L., and Gokel G.W. J. Org. Chem. 55 (1990) 2269-2270
114. Illuminati G., Mandolini L., and Masci B. J. Am. Chem. Soc. 105 (1983) 555-563
115. Yoo H.K., Davis D.M., Chen Z., Echegoyen L., and Gokel G.W. Tetrahedron Lett. 31 (1990) 55-58
116. Cacciapaglia R., and Mandolini L. Chem. Soc. Rev. 22 (1993) 221-231
117. Cacciapaglia R., and Mandolini L. Pure Appl. Chem. 65 (1993) 533-538
118. Cacciapaglia R., Mandolini L., and Romolo F.S. J. Phys. Org. Chem. 5 (1992) 457-460
119. Ercolani G., and Mandolini L. J. Am. Chem. Soc. 112 (1990) 423-427
120. Cacciapaglia R., Lucente S., Mandolini L., Van Doorn A.R., Reinhoudt D.N., and Verboom W. Tetrahedron 45 (1989) 5293-5304
121. Cacciapaglia R., Mandolini L., Reinhoudt D.N., and Verboom W. J. Phys. Org. Chem. 5 (1992) 663-669
122. Kraft D., Cacciapaglia R., Boehmer V., Abu El-Fadl A., Harkema S., Mandolini L., Reinhoudt D.N., Verboom W., and Vogt W. J. Org. Chem. 57 (1992) 826-834
123. Brandt K., Siwy M., Porwolik-Czomperlik I., and Stilberring J. J. Org. Chem. 66 (2001) 5701-5712
124. Hanessian S., Kagotani M., and Komaglou K. Heterocycles 28 (1989) 1115-1120
125. Hanessian S., and Johnstone S. J. Org. Chem. 71 (1999) 3285-3286
126. Gobbi A., Landini D., Maia A., and Secci D. J. Org. Chem. 60 (1995) 5954-5957
127. Gobbi A., Landini D., Maia A., and Penso M. J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. 11 (1996) 2505-2509
128. Albanese D., Landini D., and Maia A. J. Org. Chem. 66 (2001) 3249-3252
129. Lepore S.D., Bhunia A.K., and Cohn P.C. J. Org. Chem. 70 (2005) 8117-8121
130. Lepore, S. D.; Mondal, D. Unpublished results.
131. Kozikowski A.P., and Lee J. Tetrahedron Lett. 29 (1988) 3053-3056 and references cited therein
132. Lepore S.D., Bhunia A.K., Mondal D., Cohn P.C., and Lefkowitz C. J. Org. Chem. 71 (2006) 3285-3286
133. Sinnott M.L., Storesund H.J., and Whiting M.C. J. Chem. Soc. D: Chem. Commun. (1969) 1000-1001
134. Lepore, S. D.; Mondal, D.; Li, S. Unpublished results.