Synthetic uses of ynolates

Tetrahedron

Volumn 63, Issue 1, 2007, Pages 10-36

  Shindo, Mitsuru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Lactones; Carbanions; Cycloaddition; Olefination; Torquoselectivity; Ynolates

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ANION; AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; KETONE; LACTONE DERIVATIVE; LITHIUM DERIVATIVE; NITRONE; SILANE DERIVATIVE; THIOESTER; YNOLATE ANION;

CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CYCLOADDITION; MICHAEL ADDITION; OLEFINATION; ORGANIC CHEMISTRY; OXYGENATION; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION KINETICS; REVIEW;

EID: 33751518128     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.013     Document Type: Review

References (155)

1. For previous reviews, see:
2. Shindo M. Chem. Soc. Rev. 27 (1998) 367
3. Shindo M. J. Synth. Org. Chem. Jpn. 58 (2000) 1155
4. Shindo M. Yakugaku Zasshi 120 (2000) 1233
5. Shindo M. Synthesis (2003) 2275
6. Schöllkopf U., and Hoppe I. Angew. Chem., Int. Ed. Engl. 14 (1975) 765
7. Hoppe I., and Schöllkopf U. Liebigs Ann. Chem. (1979) 219
8. For reviews on ketenes, see:
9. Tidwell T.T. Angew. Chem., Int. Ed. 44 (2005) 6812
10. Orr R.K., and Calter M.A. Tetrahedron 59 (2003) 3545
11. Far A.R. Angew. Chem., Int. Ed. 42 (2003) 2340
12. Palomo C., Aizpurua J.M., Ganboa I., and Oiarbide M. Eur. J. Org. Chem. (1999) 3223
13. Sato M., and Iwamoto K. J. Synth. Org. Chem. Jpn. 57 (1999) 76
14. Pommier A., Kocienski P., and Pons J.-M. J. Chem. Soc., Perkin Trans. 1 (1998) 2105
15. Tidwell T.T. Ketenes (1995), Wiley, New York, NY
16. Wentrup C., Heilmayer W., and Kollenz G. Synthesis (1994) 1219
17. Hyatt J.A., and Raynolds P.W. Org. React. 45 (1994) 159
18. Tidwell T.T. Acc. Chem. Res. 23 (1990) 273
19. Snider B.B. Chem. Rev. 88 (1988) 793
20. Seikaly H.R., and Tidwell T.T. Tetrahedron 42 (1986) 2587
21. Woodbury R.P., Long N.R., and Rathke M.W. J. Org. Chem. 43 (1978) 376
22. Akai S., Kitagaki S., Naka T., Yamamoto K., Tsuzuki Y., Matsumoto K., and Kita Y. J. Chem. Soc., Perkin Trans. 1 (1996) 1705
23. Ito M., Shirakawa E., and Takaya H. Synlett (2002) 1329
24. Kai H., Iwamoto K., Chatani N., and Murai S. J. Am. Chem. Soc. 118 (1996) 7634
25. Kowalski C.J., and Fields K.W. J. Am. Chem. Soc. 104 (1982) 321
26. Kowalski C.J., Haque M.S., and Fields K.W. J. Am. Chem. Soc. 107 (1985) 1429
27. Kowalski C.J., and Reddy R.E. J. Org. Chem. 57 (1992) 7194
28. Reddy R.E., and Kowalski C.J. Org. Synth. 71 (1993) 146
29. Suau R., Lópes-Romero J.M., Rico R., Alonso F.J., and Lobo C. Tetrahedron 52 (1996) 11307
30. Gray D., Concellon C., and Gallagher T. J. Org. Chem. 69 (2004) 4849
31. Nakata T., Kuwabara T., Tani Y., and Oishi T. Tetrahedron Lett. 23 (1982) 1015
32. Satoh T., Nakamura A., Iriuchijima A., Hayashi Y., and Kubota K. Tetrahedron 57 (2001) 9689
33. Satoh T., Unno H., Mizu Y., and Hayashi Y. Tetrahedron 53 (1997) 7843
34. Satoh T., Mizu Y., Hayashi Y., and Yamakawa K. Tetrahedron Lett. 35 (1994) 133
35. Stang P.J., and Surber B.W. J. Am. Chem. Soc. 107 (1985) 1452
36. Stang P.J., and Roberts K. J. Am. Chem. Soc. 108 (1986) 7125
37. Hill J.G., Rossiter B.E., and Sharpless K.B. J. Org. Chem. 48 (1983) 3607
38. Julia M., Saint-Jalmes V.P., and Verpeaux J.N. Synlett (1993) 233
39. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 10204
40. Camici L., Dembech P., Ricci A., Seconi G., and Taddei M. Tetrahedron 44 (1988) 4197
41. Florio S., and Troisi L. Tetrahedron Lett. 34 (1993) 3141
42. Häner R., Laube T., and Seebach D. J. Am. Chem. Soc. 107 (1985) 5396
43. Tomioka K., Shindo M., and Koga K. J. Org. Chem. 55 (1990) 2276
44. Shindo M. Tetrahedron Lett. 38 (1997) 4433
45. Shindo M., Sato Y., and Shishido K. Tetrahedron 54 (1998) 2411
46. Shindo, M.; Matsumoto, K.; Shishido, K. Org. Synth., in press.
47. Shindo M., Sato Y., Koretsune R., Yoshikawa T., Matsumoto K., Itoh K., and Shishido K. Chem. Pharm. Bull. 51 (2003) 477
48. Chen C., Liao Y., and Huang Y. Tetrahedron 45 (1989) 3011
49. Yus M., Herrera R.P., and Guijarro A. Chem.-Eur. J. 8 (2002) 2574 For reviews, see:
50. Yus M. Synlett (2001) 1197
51. Ramon D.J., and Yus M. Eur. J. Org. Chem. (2000) 225
52. Yus M. Chem. Soc. Rev. (1996) 155
53. Shindo M., Koretsune R., Yokota W., Itoh K., and Shishido K. Tetrahedron Lett. 42 (2001) 8357
54. Groh B.L., Magrum R.R., and Barton T.J. J. Am. Chem. Soc. 109 (1987) 7568
55. Shindo M., Sato Y., and Shishido K. J. Am. Chem. Soc. 121 (1999) 6507
56. Shindo M., Sato Y., and Shishido K. J. Org. Chem. 66 (2001) 7818
57. Shindo M., Sato Y., and Shishido K. Tetrahedron Lett. 43 (2002) 5039
58. Shindo M., Matsumoto K., Sato Y., and Shishido K. Org. Lett. 3 (2001) 2029
59. Mulzer J., and Kerkmann T. J. Am. Chem. Soc. 102 (1980) 3620
60. Shindo M., Sato Y., and Shishido K. Tetrahedron Lett. 39 (1998) 4857
61. Shindo M., Sato Y., Yoshikawa T., Koretsune R., and Shishido K. J. Org. Chem. 69 (2004) 3912
62. Shindo M., Sato Y., and Shishido K. J. Org. Chem. 65 (2000) 5443
63. For theoretical calculations for the ring opening of oxetene, see:. Yu H., Chan W.-T., and Goddard J.D. J. Am. Chem. Soc. 112 (1990) 7529
64. Niwayama S., Kallel E.A., Spellmeyer D.C., Sheu C., and Houk K.N. J. Org. Chem. 61 (1996) 2813 For a review, see:
65. Dolbier Jr. W.R., Koroniak H., Houk K.N., and Sheu C. Acc. Chem. Res. 29 (1996) 471
66. Curry M.J., and Stevens D.R. J. Chem. Soc., Perkin Trans. 2 (1980) 1391
67. Dolbier Jr. W.R., Koroniak H., Burton D.J., Bailey A.R., Shaw G.S., and Hansen S.W. J. Am. Chem. Soc. 106 (1984) 1871
68. Kirmse W., Rondan N.G., and Houk K.N. J. Am. Chem. Soc. 106 (1984) 7989
69. Rondan N.G., and Houk K.N. J. Am. Chem. Soc. 107 (1985) 2099
70. Mori, S.; Shindo, M. Unpublished results.
71. For recent discussions, see:
72. Murakami M., Miyamoto Y., and Ito Y. Angew. Chem., Int. Ed. 40 (2001) 189
73. Lee P.S., Zhang X., and Houk K.N. J. Am. Chem. Soc. 125 (2003) 5072
74. Alabugin I.V., and Zeidan T.A. J. Am. Chem. Soc. 124 (2002) 3175
75. Mori S., and Shindo M. Org. Lett. 6 (2004) 3945
76. For recent reviews, see:
77. Miura K., and Hosomi A. Synlett (2003) 143
78. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063
79. For reviews, see:
80. Najera C., and Yus M. Org. Prep. Proced. Int. 27 (1995) 383
81. Bulman Page P.C., Klair S.S., and Rosenthal S. Chem. Soc. Rev. 19 (1990) 147
82. Ricci A., and Degl'Innocenti A. Synthesis (1989) 647
83. For disubstituted silylalkenes via the Wittig reaction and Peterson olefination, see:
84. Anderson C.L., Soderquist J.A., and Kabalka G.W. Tetrahedron Lett. 33 (1992) 6915
85. Larson G.L., Soderquist J.A., and Claudio M.R. Synth. Commun. 20 (1990) 1095
86. Soderquist J.A., and Anderson C.L. Tetrahedron Lett. 29 (1988) 2425
87. Soderquist J.A., and Anderson C.L. Tetrahedron Lett. 29 (1988) 2777
88. Shindo M., Matsumoto K., Mori S., and Shishido K. J. Am. Chem. Soc. 124 (2002) 6840
89. Taguchi H., Ghoroku K., Tadaki M., Tsubouchi A., and Takeda T. Org. Lett. 3 (2001) 3811
90. Miller R.B., and Reichenbach T. Tetrahedron Lett. (1974) 543
91. Shindo M., Matsumoto K., and Shishido K. Angew. Chem., Int. Ed. 43 (2004) 104
92. Shindo M., Matsumoto K., and Shishido K. Synlett (2005) 176
93. Shindo M., Matsumoto K., and Shishido K. Chem. Commun. (2005) 2477
94. Shindo M., Yoshikawa T., Itou Y., Mori S., Nishii T., and Shishido K. Chem.-Eur. J. 12 (2006) 524
95. Shindo M., Kita T., Kumagai T., Matsumoto K., and Shishido K. J. Am. Chem. Soc. 128 (2006) 1062
96. For examples of recent reviews, see:
97. Taggi A.E., Hafez A.M., and Lectka T. Acc. Chem. Res. 36 (2003) 10
98. Alvaro G., and Savoia D. Synlett (2002) 651
99. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984
100. Adams J.P. J. Chem. Soc., Perkin Trans. 1 (2000) 125
101. Adlington R.M., Barrett A.G.M., Quayle P., and Walker A. J. Chem. Soc., Chem. Commun. (1981) 404
102. Barrett A.G.M., and Quayle P. J. Chem. Soc., Perkin Trans. 1 (1982) 2193
103. Shindo M., Oya S., Sato Y., and Shishido K. Heterocycles 49 (1998) 113
104. Shindo M., Oya S., Murakami R., Sato Y., and Shishido K. Tetrahedron Lett. 41 (2000) 5943
105. For the acceleration of addition of lithium ester enolates to aldimines, see:. Saito S., Hatanaka K., and Yamamoto H. Org. Lett. 2 (2000) 1891
106. Shindo M., Oya S., Murakami R., Sato Y., and Shishido K. Tetrahedron Lett. 41 (2000) 5947
107. For a review on isocyanates, see:. Ozaki S. Chem. Rev. 72 (1972) 457
108. Shindo M., Harada A., Matsumoto K., and Shishido K. Heterocycles 66 (2005) 39
109. For recent reviews, see:
110. In: Padwa A., and Pearson W.H. (Eds). Chemistry of Heterocyclic Compounds Vol. 58 (2002), Wiley, New York, NY
111. Osborn H.M.I., Gemmell N., and Harwood L.M. J. Chem. Soc., Perkin Trans. 1 (2002) 2419
112. Gothelf K.V., and Jorgensen K.A. Chem. Commun. (2000) 1449
113. In: Kobayashi S., and Jorgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis (2002), Pergamon, Oxford
114. Shindo M., Itoh K., Tsuchiya C., and Shishido K. Org. Lett. 4 (2002) 3119
115. Shindo M., Itoh K., Ohtsuki K., Tsuchiya C., and Shishido K. Synthesis (2003) 1441
116. Shindo M., Ohtsuki K., and Shishido K. Tetrahedron: Asymmetry 16 (2005) 2821
117. Iwamoto K., Kojima M., Chatani N., and Murai S. J. Org. Chem. 66 (2001) 169
118. Austin W.F., Zhang Y., and Danheiser R.L. Org. Lett. 7 (2005) 3905
119. Kowalski C.J., and Haque M.S. J. Am. Chem. Soc. 108 (1986) 1325
120. Kowalski C.J., and Lal G.S. J. Am. Chem. Soc. 108 (1986) 5356
121. Kowalski C.J., and Lal G.S. Tetrahedron Lett. 28 (1987) 2463
122. Pi R., Friedl T., Schleyer P.v.R., Klusener P., and Brandsma L. J. Org. Chem. 52 (1987) 4299
123. Kowalski C.J., Lal G.S., and Haque M.S. J. Am. Chem. Soc. 108 (1986) 7127
124. Danheiser R.L., and Helgason A.L. J. Am. Chem. Soc. 116 (1994) 9471
125. Sweis R.F., Schramm M.P., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 7442
126. Maas G., and Brückmann R. J. Org. Chem. 50 (1985) 2801
127. Brückmann R., Schneider K., and Maas G. Tetrahedron 45 (1989) 5517
128. Danheiser R.L., Nishida A., Savariar S., and Trova M.P. Tetrahedron Lett. 29 (1988) 4917
129. Kowalski C.J., and Sakdarat S. J. Org. Chem. 55 (1990) 1977
130. Shindo M., Oya S., Sato Y., and Shishido K. Heterocycles 52 (2000) 545
131. Danheiser R.L., and Gee S.K. J. Org. Chem. 49 (1984) 1672
132. Kowalski C.J., and Lal G.S. J. Am. Chem. Soc. 110 (1988) 3693
133. Danheiser R.L., Casebier D.S., and Loebach J.L. Tetrahedron Lett. 33 (1992) 1149
134. Danheiser R.L., and Cha D.D. Tetrahedron Lett. 31 (1990) 1527
135. Danheiser R.L., Casebier D.S., and Huboux A.H. J. Org. Chem. 59 (1994) 4844
136. Danheiser R.L., and Trova M.P. Synlett (1995) 573
137. Danheiser R.L., Casebier D.S., and Firooznia F. J. Org. Chem. 60 (1995) 8341
138. Smith III A.B., Kozmin S.A., and Paone D.V. J. Am. Chem. Soc. 121 (1999) 7423
139. Smith III A.B., Kozmin S.A., Adams C.M., and Paone D.V. J. Am. Chem. Soc. 122 (2000) 4984
140. Smith III A.B., Adams C.M., Kozmin S.A., and Paone D.V. J. Am. Chem. Soc. 123 (2001) 5925
141. For recent reviews, see:
142. Diver S.T., and Giessert A.J. Chem. Rev. 104 (2004) 1317
143. Poulsen R.H., and Madsen R. Synthesis (2003) 1
144. Schramm M.P., Reddy D.S., and Kozmin S.A. Angew. Chem., Int. Ed. 40 (2001) 4274
145. Reddy D.S., and Kozmin S.A. J. Org. Chem. 69 (2004) 4860
146. For reviews, see:
147. Ficini J. Tetrahedron 32 (1976) 1449
148. Zificsak C.A., Mulder J.A., Hsung R.P., Rameshkumar C., and Wei L.-l. Tetrahedron 57 (2001) 7575
149. Narasaka K., Hayashi Y., Shimadzu H., and Niihata S. J. Am. Chem. Soc. 114 (1992) 8869
150. Ito H., Hasegawa M., Takenaka Y., Kobayashi T., and Iguchi K. J. Am. Chem. Soc. 126 (2004) 4520
151. Koketsu M., Mizutani K., Ogawa T., Takahashi A., and Ishihara H. J. Org. Chem. 69 (2004) 8938
152. For an example, see:. Nishizawa M., Takao H., Yadav V., Imagawa H., and Sugihara T. Org. Lett. 5 (2003) 4563
153. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 11806
154. Nieto-Oberhuber C., Munoz M.P., Bunuel E., Nevado C., Cardenas D.J., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 2402
155. Mamane V., Gress T., Krause H., and Fürstner A. J. Am. Chem. Soc. 126 (2004) 8654