Recent applications of α-amido sulfones as in situ equivalents of activated imines for asymmetric catalytic nucleophilic addition reactions

Synthesis

Volumn , Issue 21, 2010, Pages 3583-3595

  Yin, Biaolin ^a   Zhang, Yuanxiu ^a   Xu, Li Wen ^b  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

amido sulfone; asymmetric catalysis; enantioselective; N acylimino derivatives; nucleophilic addition

Indexed keywords

AMIDO SULFONES; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE; N-ACYLIMINO DERIVATIVES; NUCLEOPHILIC ADDITIONS;

AMIDES; AMINES; CATALYSIS; ORGANOMETALLICS; SULFUR COMPOUNDS;

ADDITION REACTIONS;

ALPHA AMIDO SULFONE DERIVATIVE; IMINE; ORGANOMETALLIC COMPOUND; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; NUCLEOPHILICITY; REVIEW; SYNTHESIS;

EID: 77958565895     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258241     Document Type: Review

References (168)

1. For examples, see:, Yamamoto Y, Asao N, Chem. Rev. 1993 93 2207
2. Enders D, Reinhold U, Tetrahedron: Asymmetry 1997 8 1895
3. Bloch R, Chem. Rev. 1998 98 1407
4. Kobayashi S, Ishitani H, Chem. Rev. 1999 99 1069
5. Liu M, Sibi M P., Tetrahedron 2002 58 7991
6. Friestad G F., Mathies A K., Tetrahedron 2007 63 2541
7. Nugent T C., El-Shazly M, Adv. Synth. Catal. 2010 352 753
8. For examples, see:, Weinreb S M., Top. Curr. Chem. 1997 190 131
9. Weinreb J A., Owens T D., Tang T P., Acc. Chem. Res. 2002 35 984
10. Zhou P, Chen B.-C, Davis F A., Tetrahedron 2004 60 8003
11. Lin G Q., Xu M H., Zhong Y W., Sun X W., Acc. Chem. Res. 2008 41 831
12. Ferreira F, Botuha C, Chemla F, Perez-Luna A, Chem. Soc. Rev. 2009 38 1162
13. For examples, see:, Weinreb S M., Orr R K., Synthesis 2005 1205
14. Spino C, Angew. Chem. Int. Ed. 2004 43 1764
15. Beresford K J. M., Tetrahedron Lett. 2004 45 6041
16. Kohmura Y, Mase T, J. Org. Chem. 2004 69 6329
17. Du Y, Xu L W., Shimizu Y, Oisaki K, Kanai M, Shibasaki M, J. Am. Chem. Soc. 2008 130 16146
18. Kaur P, Shaky G, Sun H, Pan Y, Li G, Org. Biomol. Chem. 2010 8 1091
19. Weinreb S M., Scola P M., Chem. Rev. 1989 89 1525
20. Petrini M, Torregiani E, Synthesis 2007 159
21. Remuson R, Gelas-Mialhe-Mialhe Y, Mini-Rev. Org. Chem. 2008 5 193; and references cited therein
22. For examples, see:, Speckamp W N., Hiemstra H, Tetrahedron 1985 41 4367
23. Hiemstra H, Speckamp W N., Comprehensive Organic Synthesis Vol. 2 Heathcock C H. Pergamon Oxford 1991 1047
24. DeKoning H, Speckamp W N., Stereoselective Synthesis (Houben-Weyl) Vol. E21 Helmchen G Hoffman R W. Mulzer J Schaumann E Georg Thieme Verlag Stuttgart 1995 1953
25. Speckamp W N., Moolenaar M J., Tetrahedron 2000 56 3817
26. Petrini M, Targets in Heterocyclic Systems Vol. 6 Attanasi O A. Spinelli D Societ Chimica Italiana Rome 2002 99
27. Pilli R A., Rosso G B., Science of Synthesis Vol. 27 Padwa A Thieme Stuttgart 2004 375
28. Maryanoff B E., Zhang H.-C, Cohen J H., Turchi I J., Maryanoff C A., Chem. Rev. 2004 104 1431
29. Yazici A, Pyne S G., Synthesis 2009 339
30. Yazici A, Pyne S G., Synthesis 2009 513
31. Zhang W, Franzen J, Adv. Synth. Catal. 2010 352 499
32. Recent examples of hydrazones 6:, Samanta D, Kargbo R B., Cook G R., J. Org. Chem. 2009 74 7183
33. Chakrabati A, Konishi H, Yamaguchi M, Schneider U, Kobayashi S, Angew. Chem. Int. Ed. 2010 49 1838
34. Recent examples of nitrones 7:, Jiao P, Nakashima D, Yamamoto H, Angew. Chem. Int. Ed. 2008 47 2411
35. Kissane M, Maguire A R., Chem. Soc. Rev. 2010 39 845; and references cited therein
36. For examples, see:, Coghlan P A., Easton C J., Tetrahedron Lett. 1999 40 4745
37. Gizecki P, Dhal R, Poulard C, Gosselin P, Dujardin G, J. Org. Chem. 2003 68 4338
38. Gizecki P, Ait-Youcef R, Poulard C, Gosselin P, Dujardin G, Tetrahedron Lett. 2004 45 9589
39. Katritzky A R., Manju K, Singh S K., Meher N K., Tetrahedron 2005 61 2555
40. Pasunooti K K., Leow M L., Vedachalam S, Gorityala B K., Liu X W., Tetrahedron Lett. 2009 50 2979
41. Li W X., Ye Y, Zhang J, Fan R H., Tetrahedron Lett. 2009 50 5536
42. Engberts J B. F. N., Strating J, Recl. Trav. Chim. Pay-Bas 1964 83 733
43. Engberts J B. F. N., Strating J, Recl. Trav. Chim. Pay-Bas 1965 84 942
44. Engberts J B. F. N., Olijnsma T, Strating J, Recl. Trav. Chim. Pay-Bas 1966 85 1211
45. Engberts J B. F. N., Olijnsma T, Strating J, Recl. Trav. Chim. Pay-Bas 1967 86 463
46. Engberts J B. F. N., Olijnsma T, Strating J, Recl. Trav. Chim. Pay-Bas 1972 91 209
47. Meijer H, Tel R M., Strating J, Recl. Trav. Chim. Pay-Bas 1973 92 72
48. Schöllkopf U, Blume E, Tetrahedron Lett. 1973 14 629
49. Weygand F, Steglich W, Chem. Ber. 1965 98 487
50. VanLeusen A M., Boerma G J. M., Helmholdt R B., Siderius H, Strating J, Tetrahedron Lett. 1972 13 2367
51. Weygand F, Steglich W, Maierhofer A, Bauer A, Chem. Ber. 1968 101 1894
52. Matthies D, Synthesis 1978 53
53. Paik S, White E H., Tetrahedron 1996 52 5303
54. Petrini M, Chem. Rev. 2005 105 3949
55. Alonso D A., Alonso E, Nájera C, Yus M, Synlett 1997 491
56. Jung D Y., Ko C H., Kim Y H., Synlett 2004 1315
57. Petrini M, Torregiani E, Tetrahedron Lett. 2006 47 3501
58. Ballini R, Palmieri A, Petrini M, Torregiani E, Org. Lett. 2006 8 4093
59. Palmieri A, Petrini M, Torregiani E, Tetrahedron Lett. 2007 48 5653
60. Kuhakam C, Tangdenpaisal K, Kongsaeree P, Prabpai S, Tuchinda P, Pohmakotr M, Reutrakul V, Tetrahedron Lett. 2007 48 2467
61. Das B, Damodar K, Chowdhury N, Saritha D, Ravikanth B, Krishnaiah M, Tetrahedron 2008 64 9396
62. Das B, Damodar K, Shashikanth B, Srinivas Y, Kalavathi I, Synlett 2008 3133
63. Xie Z F., Chai Z, Zhao G, Wang J D., Synthesis 2008 3805
64. Ollevier T, Li Z Y., Adv. Synth. Catal. 2009 351 3251
65. Kadam S T., Thirupathi P, Kim S S., Tetrahedron 2009 65 10383
66. Thirupathi P, Kim S S., J. Org. Chem. 2009 74 7755
67. Das B, Damodar K, Bhunia N, J. Org. Chem. 2009 74 5607
68. Selected examples, see:, Notz W, Tanaka F, Barbas C F., Acc. Chem. Res. 2004 37 580
69. Córdova A, Acc. Chem. Res. 2004 37 102
70. Shibasaki M, Matsunaga S, J. Organomet. Chem. 2006 691 2089
71. Enders D, Vrettou M, Synthesis 2006 2155
72. Verkade J M. M., VanHemert L J. C., Quaedflieg P J. L. M., Rutjes F P. J. T., Chem. Soc. Rev. 2008 37 29
73. Xu L W., Luo J, Lu Y, Chem. Commun. 2009 1807
74. Arrayas R G., Carretero J C., Chem. Soc. Rev. 2009 38 1940
75. Kleinmann E F., Comprehensive Organic Synthesis Vol. 2 Trost B M. Fleming I Pergamon New York 1991 893-951
76. Arend M, Westermann B, Risch N, Angew. Chem. Int. Ed. 1998 37 1044
77. Palomo C, Oiarbide M, González-Rego M C., Sharma A K., Garciá J M., González A, Landa C, Linden A, Angew. Chem. Int. Ed. 2000 39 1063
78. Wang J, Shi T, Deng G, Jiang H, Liu H, J. Org. Chem. 2008 73 8563
79. Enders D, Oberbörsch S, Synlett 2002 471
80. Pesenti C, Bravo P, Corradi E, Frigerio M, Meille S V., Panzeri W, Viani F, Zanda M, J. Org. Chem. 2001 66 5637
81. Pesenti C, Arnone A, Arosio P, Frigerio M, Meille S V., Panzeri W, Viani F, Zanda M, Tetrahedron Lett. 2004 45 5125
82. Fini F, Bernardi L, Herrera R P., Pettersen D, Ricci A, Sgarzani V, Adv. Synth. Catal. 2006 348 2043
83. Mariannacci O, Micheletti G, Bernardi L, Fini F, Fochi M, Pettersen D, Sgarzani V, Ricci A, Chem. Eur. J. 2007 13 8338
84. Mizuta S, Shibata N, Goto Y, Furukawa T, Nakamura S, Toru T, J. Am. Chem. Soc. 2007 129 6394
85. For reviews on the vinylogous Mannich reaction, see
86. Casiraghi G, Zanardi F, Appendino G, Rassu G, Chem. Rev. 2000 100 1929
87. Martin S F., Acc. Chem. Res. 2002 35 895
88. Iu T.-Y, Cui H.-l, Long J, Li B.-J, Wu Y, Ding L.-S, Chen Y.-C, J. Am. Chem. Soc. 2007 129 1878
89. Carswell E L., Snapper M L., Hoveyda A H., Angew. Chem. Int. Ed. 2006 45 7230
90. Niess B, Jørgensen A, Chem. Commun. 2007 1620
91. Yamaguchi A, Aoyama N, Matsunaga S, Shibasaki M, Org. Lett. 2007 9 3387
92. Utsuml N, Kitagaki S, Barbas C F., Org. Lett. 2008 10 3405
93. Cassani C, Bernardi L, Fini F, Ricci A, Angew. Chem. Int. Ed. 2009 48 5694
94. Momo R D., Fini F, Bernardi A, Ricci A, Adv. Synth. Catal. 2009 351 2283
95. Aminophosphonic and Aminophosphinic Acids Kukhar V P. Hudson H R. John Wiley & Sons New York 2000
96. Ma J A., Chem. Soc. Rev. 2006 35 630
97. Naydenova E D., Todorov P T., Troev K D., Amino Acids 2010 38 23
98. González P B., Lopez R, Palomo C, J. Org. Chem. 2010 75 3920
99. Selected reviews, see:, Mukherjee S, Yang J W., Hoffmann S, List B, Chem. Rev. 2007 107 5471
100. Erkkilä A, Majander I, Pihko P M., Chem. Rev. 2007 107 5416
101. Xu L W., Lu Y, Org. Biomol. Chem. 2008 6 2047
102. Zhang Z G., Schreiner P R., Chem. Soc. Rev. 2009 38 1187
103. Bhadury P S., Song B A., Yang S, Hu D Y., Xue W, Curr. Org. Synth. 2009 6 380
104. Xu L W., Li L, Shi Z H., Adv. Synth. Catal. 2010 352 243
105. Song J, Shi H W., Deng L, Org. Lett. 2007 9 603
106. Lou S, Dai P, Schaus S E., J. Org. Chem. 2007 72 9998
107. Goss M, Schaus S E., J. Org. Chem. 2008 73 7651
108. Gianelli C, Sambri L, Carlone A, Bartoli G, Melchiorre P, Angew. Chem. Int. Ed. 2008 47 8700
109. Galzerano P, Agostino D, Bencivenni G, Sambri L, Bartoli G, Melchiorre P, Chem. Eur. J. 2010 16 6069
110. Deiana L, Zhao G.-L, Dziedzic P, Rios R, Vesely J, Ekstrom J, Córdova A, Tetrahedron Lett. 2010 51 234
111. Takada K, Tanaka S, Nagasawa K, Synlett 2009 1643
112. ODonnell M J., Bennett W D., Wu S, J. Am. Chem. Soc. 1989 111 2353
113. ODonnell M J., Acc. Chem. Res. 2004 37 506
114. Maruoka K, Ooi T, Chem. Rev. 2003 103 3013
115. Lygo B, Andrews B I., Acc. Chem. Res. 2004 37 518
116. Zhang H, Syed S, Barbas C F., Org. Lett. 2010 12 708
117. Alvaro G, Savoia D, Synlett 2002 651
118. Bräse S, Baumann T, Dahmen S, Vogt H, Chem. Commun. 2007 1881
119. Fujihara H, Nagai K, Tomioka K, J. Am. Chem. Soc. 2000 122 12055
120. Lombardo M, Mosconi E, Pasi F, Petrini M, Trombini C, J. Org. Chem. 2007 72 1834
121. Porter J R., Traverse J F., Hoveyda A H., Snapper M L., J. Am. Chem. Soc. 2001 123 984
122. Porter J R., Traverse J F., Hoveyda A H., Snapper M L., J. Am. Chem. Soc. 2001 123 10409
123. Dahmen S, Bräse S, J. Am. Chem. Soc. 2002 124 5940
124. Hermanns N, Dahmen S, Bolm C, Bräse S, Angew. Chem. Int. Ed. 2002 41 3692
125. Boezio A A., Charette A, J. Am. Chem. Soc. 2003 125 1692
126. Côté A, Boezio A A., Charette A B., Proc. Natl. Acad. Sci. U.S.A. 2004 101 5405
127. Desrosiers J.-N, Côté A, Charette A B., Tetrahedron 2005 61 6186
128. Bonnaventure I, Charette A B., Tetrahedron 2009 65 4968
129. Zhang H.-L, Liu H, Cui X, Mi A.-Q, Jiang Y.-Z, Gong L.-Z, Synlett 2005 615
130. Liu H, Zhang H.-L, Wang S.-J, Mi A.-Q, Jiang Y.-Z, Gong L.-Z, Tetrahedron: Asymmetry 2005 16 2901
131. Pizzuti M G., Minnaard A J., Feringa B L., J. Org. Chem. 2008 73 940
132. Selected reviews, see:, Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
133. Zhou S L., Xu L W., Xia C G., Li J W., Li F W., Chin. J. Org. Chem. 2004 24 1501
134. Miyaura N, Synlett 2009 2039
135. Ueda M, Saito A, Miyaura N, Synlett 2000 1637
136. Nakagawa H, Rech J C., Sindelar R W., Ellman J A., Org. Lett. 2007 9 5155
137. Westermann B, Angew. Chem. Int. Ed. 2003 42 151
138. Marques E, Merino P, Tejero T, Herrera R P., Eur. J. Org. Chem. 2009 2401
139. Fini F, Sgarzani V, Pettersen D, Herrera R P., Bernardi L, Ricci A, Angew. Chem. Int. Ed. 2005 44 7975
140. Palomo C, Oiarbide M, Laso A, López R, J. Am. Chem. Soc. 2005 127 17622
141. Gomez-Bengoa E, Linden A, López R, Múgica-Mendiola I, Oiarbide M, Palomo C, J. Am. Chem. Soc. 2008 130 7955
142. Jiang X, Zhang Y, Wu L, Zhang G, Liu X, Zhang H, Fu D, Wang R, Adv. Synth. Catal. 2009 351 2096
143. Selected recent reviews, see:, Vogt H, Bräse S, Org. Biomol. Chem. 2007 5 406
144. Pastori N, Gambarotti C, Punta C, Mini-Rev. Org. Chem. 2009 6 184
145. Herrera R P., Sgarzani V, Bernardi L, Fini F, Pettersen D, Ricci A, J. Org. Chem. 2006 71 9869
146. Ooi T, Uematsu Y, Fujimoto J, Fukumoto K, Maruoka K, Tetrahedron Lett. 2007 48 1337
147. Reingruber R, Baumann T, Dahmen S, Bräse S, Adv. Synth. Catal. 2009 351 1019
148. Murry J A., Frantz D E., Soheili A, Tillyer R, Grabowski E J. J., Reider P J., J. Am. Chem. Soc. 2001 123 9696
149. Mennen S M., Gipson J D., Kim Y R., Miller S J., J. Am. Chem. Soc. 2005 127 1654
150. Fini F, Micheletti G, Bernardi L, Pettersen D, Fochi M, Ricci A, Chem. Commun. 2008 4345
151. Kamimura A, Gunjigake Y, Mitsudera H, Yokoyama S, Tetrahedron Lett. 1998 39 7323
152. Shi Y L., Shi M, Eur. J. Org. Chem. 2007 2905
153. Declerck V, Martinez J, Lamaty F, Chem. Rev. 2009 109 1
154. Č;íhalová S, Remes M, Cisaová I, Vesely J, Eur. J. Org. Chem. 2009 6277
155. Abermil N, Masson G, Zhu J, Adv. Synth. Catal. 2010 352 656
156. Mazzotta S, Gramigna L, Bernardi L, Ricci A, Org. Process Res. Dev. 2010 14 687
157. Fruhauf H W., Coord. Chem. Rev. 2002 230 79
158. Melo P, Teresa M V. D., Curr. Org. Chem. 2009 13 1406
159. Gioia C, Fini F, Mazzanti A, Bernardi L, Ricci A, J. Am. Chem. Soc. 2009 131 9614
160. Friot C, Reliquet A, Reliquet F, Meslin J C., Synthesis 2000 695
161. Bharatam V, Kumar R S., Mahajan M P., Org. Lett. 2000 2 2725
162. Abraham C J., Paull D H., Scerba M T., Grebinski J W., Lectka T, J. Am. Chem. Soc. 2006 128 13370
163. Cossio F P., Arrieta A, Sierra M A., Acc. Chem. Soc. 2008 41 925
164. Xu X, Wang K, Nelson S G., J. Am. Chem. Soc. 2007 129 11690
165. Miyabe H, Yoshioka E, Kohtani S, Curr. Org. Chem. 2010 14 1254
166. Reddy L R., Prashad M, Chem. Commun. 2010 222
167. Dickstein J S., Kozlowski M C., Chem. Soc. Rev. 2008 37 1166
168. Vilaivan T, Bhanthumnavin W, Sritana-Anant Y, Curr. Org. Chem. 2005 9 1315