Multiple stereoselectivity and its application in organic synthesis

Tetrahedron

Volumn 59, Issue 32, 2003, Pages 5953-6018

  Kolodiazhnyi, Oleg I ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

Chiral catalysts; Double asymmetric synthesis; Multiple stereochemical control; Multiple stereoselectivity

Indexed keywords

ACETOGENIN; ALKENE DERIVATIVE; ALLYL ALCOHOL; AMPHIDINOLIDE B; AMPHOTERICIN B; BOROMYCIN; CASTANOSPERMINE; CINNAMIC ACID DERIVATIVE; CYCLOBUTANE DERIVATIVE; DIHYDROQUINIDINE; DIPEPTIDE DERIVATIVE; ETHER DERIVATIVE; HALICHONDRIN B; HEPTANOIC ACID DERIVATIVE; IMINE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; MACROLIDE; ORGANIC COMPOUND; PALLADIUM COMPLEX; PARVIFLORIN; PHTHALAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; QUINUCLIDINE DERIVATIVE; RHAMNOSE; STEROID; TACROLIMUS; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZIRCONIUM DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ALKYLATION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONJUGATION; CYCLOADDITION; DIELS ALDER REACTION; DIHYDROXYLATION; DRUG SYNTHESIS; EPOXIDATION; HYDROBORATION; HYDROGENATION; HYDROSILYLATION; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0041344683     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00911-6     Document Type: Review

References (372)

1. Ward R.S. Selectivity in Organic Synthesis. 1999;Wiley, Chichester. pp 1-165.
2. Nogradi M. Stereoslective Synthesis. 2nd ed. 1995;VCH, Weinheim. Chapter 1.
3. Atta-ur-Rahman, Shah Z. Stereoselective Synthesis in Organic Synthesis. 1993;Springer, New York. pp 1-508.
4. Procter G. Asymmetric Synthesis. 1996;Oxford University, Oxford.
5. Kolodiazhnyi O.I. Hassner A. Advances in Asymmetric Synthesis. Vol. 3:1998;273-357 JAI, Stamford.
6. Vavon G., Antonini A. C. R. Acad. Sci. 230:1950;1870-1872.
7. Harada K., Matsumoto K. J. Org. Chem. 31:1966;2985-2991.
8. Horeau A., Kagan H.B., Vigneron J.P. Bull. Soc. Chim. Fr. 1968;3795-3797.
9. Izumi Y., Tai A. Stereodifferentiating Reactions. 1977;Academic Press, New York.
10. Poulin J.-C., Kagan H.B. J. Chem. Soc., Chem. Commun. 1982;1261-1262.
11. Heathcock C.H. Morrison J.D. Asymmetric Synthesis. Vol. 3:1984;191-206 Academic, New York.
12. Masamune S., Choy W., Peterson J.S., Sita L.R. Angew. Chem. 97:1985;1-31. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30.
13. Vineyard B.V., Knowles W.S., Sabacky M.J., Bachman G.L., Weinkauff O.J. J. Am. Chem. Soc. 99:1977;5946-5952.
14. Seydenne-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis. 1995;Wiley, New York. pp 36-41.
15. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., Galvez J.A. Tetrahedron. 55:1999;7601-7612.
16. (a) Brunner H., Tracht T. Tetrahedron: Asymmetry. 9:1998;3763-3771.
17. (b) Brunner H., Wagenhuber L. J. Organomet. Chem. 525:1996;259-268
18. (c) Cobb A.J.A., Marson M.S. Tetrahedron: Asymmetry. 12:2001;1547-1550.
19. (a) Solladie G. Morrison J.D. Asymmetric Synthesis. Vol. 2:1983;157-199 Academic, New York,
20. (b) Avalos M., Babiano R., Cintas P., Jimenes J.L., Palacios J.C. Chem. Rev. 98:1998;2391-2404,
21. (c) Seebach D., Hungerbuhler E. Scheffold R. Modern Synthetic Methods. 1980;Salle/Sauerlander, Frankfurt und Aarau
22. (d) Marchand-Brynaert J. Chimie Nouvelle. 9:1991;1007-1011.
23. Heathcock C.H., White C.T., Morrison J.J., Van Derveer D. J. Org. Chem. 46:1981;1296-1309.
24. (a) Guifa S., Lingchong Y. Synth. Commun. 23:1993;1229-1234.
25. (b) Sawamuura M., Nakayama Y., Tang W.M., Ito Y. J. Am. Chem. Soc. 114:1992;2586-2592.
26. Guette J.P., Horeau A. Bull. Soc. Chim. Fr. 1967;1747-1752.
27. Roush W.R., Hoong L.K., Palmer M.A.J., Straub J.A., Palkowitz A.D. J. Org. Chem. 55:1990;4117-4126.
28. El-Baba S., Nuzillard J.M., Poulin J.C., Kagan H.B. Tetrahedron. 42:1986;3851-3862.
29. Glaser R., Geresh S., Blumenfeld J., Vainas B., Twaik M. Isr. J. Chem. 15:1977;17.
30. Berens U., Fischer C., Selke R. Tetrahedron: Asymmetry. 6:1995;1105-1108.
31. Yamagishi T., Ikeda S., Egawa T., Yamaguchi M., Hida M. Bull. Chem. Soc. Jpn. 63:1990;281-283.
32. Yatagai M., Yamagishi T., Hida M. Bull. Chem. Soc. Jpn. 57:1984;823-826.
33. Ojima I., Tetsuo K., Yoda N., Suzuki T., Yatabe M., Tanaka T. J. Org. Chem. 47:1982;1329-1334.
34. Rowlands G.J. Tetrahedron. 57:2001;1865-1882.
35. Ojima I., Yatabe M. Chem. Lett. 1982;1335-1338.
36. Aguado G.P., Alvarez-Larena A., Ona I., Moglioni A.G., Ortuno R.M. Tetrahedron: Asymmetry. 12:2001;25-28.
37. Sunjic V., Habus I., Comisso G., Moimas F. Gazz. Chim. Ital. 119:1989;229-234.
38. Tani K., Suwa K., Tanigawa E., Ise T., Yamagata T. J. Organomet. Chem. 370:1989;203-222.
39. (a) Kitazume T., Ishikawa N. Chem. Lett. 1984;587-590
40. (b) Shagidullin R.R., Chernova A.V., Plyamovatyi A.K., Shagidullin R.R. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.). 38:1989;638-641.
41. Tungler A., Furcht A., Karancsi Z.P., Toth G., Mathe T., Hegedus L., Sandi A. J. Mol. Catal. A: Chem. 139:1999;239-244.
42. Karpeiskaya I.E., Godunova L.F., Levitina E.S., Lyubeznova M.R., Klabunovskii E.I. Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.). 41:1992;1858-1867.
43. Schmidt U., Lieberknecht A., Kazmaier U., Griesser H., Jung G., Metzger J. Synthesis. 1991;49-55.
44. (a) Ager D.J., Laneman S.A. Tetrahedron: Asymmetry. 8:1997;3237-3355.
45. (b) Fryzuk M.B., Bosnich B. J. Am. Chem. Soc. 101:1979;3043-3049.
46. (c) Riley D.P., Shumate R.E. J. Org. Chem. 45:1980;5187
47. (d) Pai C.-C., Li Y.-M., Zhou Z.Y., Chan A.S.C. Tetrahedron Lett. 43:2002;2789-2792.
48. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., Noyori R. J. Am. Chem. Soc. 102:1980;7932-7934.
49. Advanced Information. On the Nobel Prize in Chemistry 2001, Kungl Vetenskapsakademien the Royal Sweden Academy of Sciences, Web Site: www.kva.se.
50. Noyori R. Asymmetric Catalysis, Inorganic Synthesis. 1994;Wiley, New York.
51. Nishi T., Kitamura M., Ohkuma T., Noyori R. Tetrahedron Lett. 29:1988;6327-6330.
52. Wu Y.D., Houx K.N. J. Am. Chem. Soc. 109:1987;908-910.
53. Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobayashi H., Akutagawa S., Ohta T., Takaya H., Noyori R. J. Am. Chem. Soc. 110:1988;629-631.
54. (a) Matsumura H., Hashigushi S., Ikariya T., Noyori R. J. Am. Chem. Soc. 119:1997;8738-8739
55. (b) Palmer M.J., Wills M. Tetrahedron: Asymmetry. 10:1999;2045-2061.
56. Shao L., Kawano H., Saburi M., Uchida Y. Tetrahedron. 49:1993;1997-2010.
57. Kitamura M., Nagai K., Hsiao Y., Noyori R. Tetrahedron Lett. 31:1990;549-552.
58. Terada M., Sayo N., Mikami K. Synlett. 1995;411-415.
59. Fehr M.J., Consiglio G., Scalone M., Schmid R. J. Org. Chem. 64:1999;5768-5776.
60. Kim J.-S., Shin-ya K., Furihata K., Hayakawa Y., Seto H. Tetrahedron Lett. 38:1997;3431-3434.
61. Le Maux P., Massonneau V., Simonneaux G. Tetrahedron. 44:1988;1409-1412.
62. Ojima I., Kogura T., Kumagai M. J. Org. Chem. 42:1977;1671-1679.
63. Ojima I., Kogura T., Nagai I. Tetrahedron Lett. 1974;1889-1892.
64. Corriu R.J.P., Moreau J.J.E. Nouv. J. Chim. 1:1977;71.
65. Ohta T., Takaya H., Noyori R. Inorg. Chem. 27:1988;566-569.
66. Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobayashi H., Akutagawa S., Otha T., Takaya H., Noyori R. J. Am. Chem. Soc. 110:1988;629-631.
67. Ojima I., Hirai K. Morrison J.D. Asymmetric Synthesis. Vol. 5:1985;103-145 Academic, New York.
68. Ohkuma T., Ooka H., Hashiguchi S., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;2675-2676.
69. Pamies O., Net G., Ruiz A., Claver C. Eur. J. Inorg. Chem. 2000;2011-2016.
70. Brown H.C., Vara Prasad J.V.N. J. Am. Chem. Soc. 108:1986;2049-2054.
71. Sailes H.E., Watts J.P., Whitinga A. Tetrahedron Lett. 41:2000;2457-2461.
72. Reiners I., Wilken J., Martens J. Tetrahedron: Asymmetry. 6:1995;3063-3070.
73. Garcia Ruano J.L., Cifuentes M.M., Lorente A., Rodriguez Ramos H.J. Tetrahedron: Asymmetry. 10:1999;4607-4618.
74. Jacobsen E.N., Marko I., Mungall W.S., Schroder G., Sharpless K.B. J. Am. Chem. Soc. 110:1988;1968-1970.
75. Zhang W., Loebach J.L., Wilson S.R., Jacobsen E.N. J. Am. Chem. Soc. 112:1990;2801-2803.
76. Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107.
77. Li G., Chang H.-T., Sharpless K.B. Angew. Chem. 108:1996;449-452.
78. O'Brien P. Angew. Chem. Int. Ed. Engl. 38:1999;326-329.
79. Tu Y., Wang Z.-X., Shi Y. J. Am. Chem. Soc. 118:1996;9806-9807.
80. (a) Frohn M., Shi Y. Synthesis. 2000;1979-2000.
81. (b) Davis F.A., Reddi R.T., Han W., Carroll P.J. J. Am. Chem. Soc. 114:1992;1428-1437.
82. Bougauchi M., Watanabe S., Arai T., Sasai H., Shibasaki M. J. Am. Chem. Soc. 119:1997;2329-2330.
83. Elston C.L., Jackson R.F.W., MacDonald S.J.F., Murray P.J. Angew. Chem. Int. Ed. Engl. 36:1997;410-412.
84. (a) Porter M.J., Skidmore J. J. Chem. Soc. Chem. Commun. 2000;1215-1226.
85. (b) Ray P.C., Roberts S.M. Tetrahedron Lett. 40:1999;1779-1782.
86. Rossiter R.E. Morrison J.D. Asymmetric Synthesis. Vol. 5:1985;194-246 Academic, New York.
87. Finn M.G., Sharpless K.B. Morrison J.D. Asymmetric Synthesis. Vol. 5:1985;247-308 Academic, New York.
88. Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 102:1980;5974-5976.
89. Sharpless K.B., Behrens C.H., Katsuki T., Lee A.W.M., Martin V.S., Takatani M., Viti S.M., Walker F.J., Woodard S.S. Pure Appl. Chem. 55:1983;589.
90. Katsuki T., Lee A.W.M., Ma P., Martin V.S., Masamune S., Sharpless K.B., Tuddenham D., Walker F.J. J. Org. Chem. 47:1982;1373-1378.
91. Ma P., Martin V.S., Masamune S., Sharpless K.B., Viti S.M. J. Org. Chem. 47:1982;1378-1380.
92. (a) Johnson R.A., Sharpless K.B. Ojima I. Catalytic Asymmetric Synthesis. 1993;103 VCH, Weinheim,
93. (b) Katsuki T., Martin V.S. Org. React. 1996;1,
94. (c) Katsuki T. Beller M., Bolm C. 1998;261 Wiley-VCH, New York,
95. (d) Katsuki T. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. II:1999;621 Springer, New York.
96. Martin V.S., Woodard S.S., Katsuki T., Yamada Y., Ikeda M., Sharpless B. J. Am. Chem. Soc. 103:1981;6237-6240.
97. Minami N., Ko S.S., Kishi Y. J. Am. Chem. Soc. 104:1982;1109-1111.
98. Roush W.R., Brown R.J. J. Org. Chem. 47:1982;1371-1373.
99. Roush W.R., Brown R.J. J. Org. Chem. 48:1983;5093-5101.
100. Finan J.M., Kishi Y. Tetrahedron Lett. 23:1982;2719-2722.
101. Vidari G., Di Rosa A., Castronovo F., Zanoni G. Tetrahedron: Asymmetry. 11:2000;981-989.
102. (a) Hoye T.R., Suhadolnik J.C. J. Am. Chem. Soc. 107:1985;5312-5313.
103. (b) Haye T.R., Suhadolnik J.C. Tetrahedron. 42:1986;2855-2862.
104. Marshall J.A., Hinkle A.W. J. Org. Chem. 61:1996;4247-4251.
105. Aube J., Wang Y., Hammond M., Tanol M., Takusagawa F., Vander Velde D. J. Am. Chem. Soc. 112:1990;4879-4891.
106. Lee A.W.M., Martin V.S., Masamune S., Sharpless K.B., Walker F.J. J. Am. Chem. Soc. 104:1982;3515-3516.
107. Cha J.K., Christ W.J., Finan J.M., Fujioka H., Kishi Y., Klein L.L., Ko S.S., Leder J., McWhorter W.W., Pfaff K.-P., Yonaga M., Uemura D., Hirata Y. J. Am. Chem. Soc. 104:1982;7369-7371.
108. Adams C.E., Walker F.J., Sharpless K.B. J. Org. Chem. 50:1985;420-422.
109. Martin C., Pruenck W., Bortolussi M., Bloch R. Tetrahedron: Asymmetry. 11:2000;1585-1592.
110. Sugimura T., Iguchi H., Tsuchida R., Tai A., Nishiyama N., Hakushi T. Tetrahedron: Asymmetry. 9:1998;1007-1013.
111. (a) Hoye T.R., Ye Z. J. Am. Chem. Soc. 118:1996;1801-1802.
112. (b) Li P., Yang J., Zhao R. J. Org. Chem. 64:1999;2259-2263.
113. Sauret S., Cuer A., Gourcy J.-G., Jeminet G. Tetrahedron: Asymmetry. 6:1995;1995-2000.
114. Rossiter B.E., Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 103:1981;464-465.
115. Keinan E., Sinha S.C., Sinha-Bagchi A., Wang Z.-M., Zhang X.-L., Sharpless K.B. Tetrahedron Lett. 33:1992;6411-6414.
116. Kotha S. Tetrahedron. 50:1994;3639-3662.
117. Meyers A.I., Hudspeth J.P. Tetrahedron Lett. 22:1981;3925-3928.
118. Masamune S., Kaiho T., Garvey D.S. J. Am. Chem. Soc. 104:1982;5521-5523.
119. Masamune S., Lu L.D.L., Jackson W.P., Kaiho T., Toyoda T. J. Am. Chem. Soc. 104:1982;5523-5526.
120. Ko S.Y., Lee A.W.M., Masamune S., Reed L.A., Sharpless K.B., Walker H.J. Science. 220:1983;949.
121. Roush W.R., Spada A.P. Tetrahedron Lett. 24:1983;3693-3696.
122. Roush W.R., Spada A.P. Tetrahedron Lett. 23:1982;3773-3776.
123. White J.D., Kang M., Sheldon B.G. Tetrahedron Lett. 24:1983;4539-4542.
124. Koizumi N., Ishiguro M., Yasuda M., Ikekawa N. J. Chem. Soc., Perkin Trans. 1. 1983;1401.
125. White J.D., Avery M.A., Choudhry S.C., Dhingra O.P., Kang M., Whittle A.J. J. Am. Chem. Soc. 105:1983;6517-6518.
126. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547.
127. Becker H., Soler M.A., Sharpless K.B. Tetrahedron. 51:1995;1345-1376.
128. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.L., Morikawa K., Wang Z.-M., Xu D., Zhang X.-L. J. Org. Chem. 57:1992;2768-2771.
129. VanNieuwenhze M.S., Sharpless K.B. J. Am. Chem. Soc. 115:1993;7864-7865.
130. Becker H., Sharpless K.B. Angew. Chem. Int. Ed. Engl. 35:1996;448-451.
131. Kolb H.C. Beller M., Bolm C. Transition Metals for Organic Synthesis. 1998;219 Wiley-VCH, New York.
132. (a) Ward R.A., Procter G. Tetrahedron. 51:1995;12821-12836.
133. (b) Ward R.A., Procter G. Tetrahedron Lett. 33:1992;3363-3366.
134. Wade P.A., Cole D.T., D'Ambrosio S.G. Tetrahedron Lett. 35:1994;53-56.
135. Sinha S.C., Keinan E. J. Org. Chem. 59:1994;949-951.
136. Hoffmann R.W., Schlapbach A. Tetrahedron Lett. 34:1993;7903-7906.
137. Gurjar M.K., Mainkar A.S., Syamala M. Tetrahedron: Asymmetry. 4:1993;2343-2346.
138. Morikawa K., Sharpless K.B. Tetrahedron Lett. 34:1993;5575-5578.
139. Brimacombe J.S., McDonald G., Rahman M.A. Carbohydr. Res. 205:1990;422-427.
140. Cha J.K., Kim N.-S. Chem. Rev. 95:1995;1761-1795.
141. Hermitage S.A., Murphy A., Nielsen P., Roberts S.M. Tetrahedron. 54:1998;13185-13202.
142. Reetz M.T., Strack T.J., Mutulis F., Goddard R. Tetrahedron Lett. 37:1996;9293-9296.
143. Burke S.D., Austad B.C., Hart A.C. J. Org. Chem. 3:1998;6770-6771.
144. Surivet J.P., Vatele J.M. Tetrahedron Lett. 39:1998;9681-9682.
145. Eng H.M., Myles D.C. Tetrahedron Lett. 40:1999;2275-2278.
146. Wang Z.-M., Tian S.-K., Shi M. Tetrahedron: Asymmetry. 10:1999;667-670.
147. Wang T.-L., Hu X.E., Cassady J.M. Tetrahedron Lett. 36:1995;9301-9304.
148. Sasaki S., Hamada Y., Shioiri T. Tetrahedron Lett. 38:1997;3013-3016.
149. Takahata H., Takahashi S., Kouno Sh.-i., Momose T. J. Org. Chem. 63:1998;2224-2231.
150. Takahata H., Kouno S., Momose T. Tetrahedron: Asymmetry. 6:1995;1085-1088.
151. Zhou W.-S., Huang L.-F., Sun L.-Q., Pan X.-F. Tetrahedron Lett. 32:1991;6745-6748.
152. McMorris T.C., Patil P.A. J. Org. Chem. 58:1993;2338-2339.
153. Sun L.-Q., Zhou W.-S., Pan X.-F. Tetrahedron: Asymmetry. 2:1991;973-976.
154. Honda T., Takada H., Miki S., Tsubuki M. Tetrahedron Lett. 34:1993;8275-8278.
155. Brosa C., Peracaula R., Puig R., Ventura M. Tetrahedron Lett. 33:1992;7057-7060.
156. Takatsuto S., Ikekawa N. Chem. Pharm. Bull. 32:1984;2001-2004.
157. Corey E.J., Grogan M.J. Tetrahedron Lett. 39:1998;9351-9354.
158. Kim N.-S., Choi J.-R., Cha J.K. J. Org. Chem. 58:1993;7096-7099.
159. Fernandes R.A., Kumar P. Synthesis. 2003;129-135.
160. (a) Fernandes R.A., Kumar P. Tetrahedron Lett. 41:2000;10309-10312.
161. (b) Fernandes R.A., Kumar P. Tetrahedron: Asymmetry. 10:1999;4349-4356.
162. Guifa S., Lingchong Y. Synth. Commun. 23:1993;1229-1234.
163. Yaozhong J., Zhou C., Piao H. Synth. Commun. 19:1989;881-888.
164. Yaozhong J., Guilan L., Zhou C., Piao H., Lanjun W., Aiqiao M. Synth. Commun. 21:1991;1087-1091.
165. Miyashita K., Miyabe H., Tai K., Iwaki H., Imanishi T. Tetrahedron. 56:2000;4691-4700.
166. Tripathy P.B., Matteson D.S. Synthesis. 3:1990;200-206.
167. Cativiella C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517-3599.
168. Genet J.P., Kopola N., Juge S., Ruiz-Montes J., Antunes O.A.C., Tanier S. Tetrahedron Lett. 31:1990;3133-3136.
169. Bajgrowicz J.A., Cossec B., Pigiere C., Jacquier R., Viallefont P. Tetrahedron Lett. 24:1983;3721-3724.
170. Beak P., Basu A., Gallagher D.J., Sun Park Y., Thayumanavan S. Acc. Chem. Res. 29:1998;552-560.
171. (a) Haller J., Hense T., Hoppe D. Liebigs Ann. 1996;489-499.
172. (b) Marr F., Froehlich R., Hoppe D. Tetrahedron: Asymmetry. 13:2002;2587-2592.
173. Torii S., Okumoto H., Kotani T., Nakayasu S., Ozaki H. Tetrahedron Lett. 33:1992;3503-3506.
174. (a) Sibi M.P., Manyem S. Tetrahedron. 56:2000;8033-8061.
175. (b) Juaristi E., Beck A.K., Hansen J., Matt T., Mukhopadhyay T., Simson M., Seebach D. Synthesis. 1993;1271-1289.
176. Brunner H., Krumey C. J. Mol. Catal. A: Chem. 142:1999;7-15.
177. Keller E., Veldman N., Spek A.L., Feringal B.L. Tetrahedron: Asymmetry. 8:1997;3403-3413.
178. Kober R., Papadopoulos K., Miltz W., Enders D., Steglich W. Tetrahedron. 41:1985;1693-1702.
179. Tran Huu Dau M.E., Riche C., Dumas F., d'Angelo J. Tetrahedron: Asymmetry. 9:1998;1059-1064.
180. Davies S.G., Hedgecock C.J.R., McKenna J.M. Tetrahedron: Asymmetry. 6:1995;827-830.
181. Takasu A., Mizutani S., Noguchi M., Makita K., Ihara M. J. Org. Chem. 65:2000;4112-4119.
182. Ishikawa T., Nagai K., Kndoh T., Saito S. Synlett. 1995;1171-1173.
183. Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389.
184. Mahrwald R. Chem. Rev. 99:1999;1095-1120.
185. Fringuelli F., Piermatti O., Pizzo F., Scappini A.-M. Gazz. Chim. Ital. 125:1995;195-200.
186. Toda F., Tanaka K., Hamai K. J. Chem. Soc. Perkin Trans. 1. 1990;3207-3209.
187. Mengel A., Reiser O. Chem. Rev. 99:1999;1191-1223.
188. Davies S.G., Shipton M.R. Synlett. 1991;25-26.
189. (a) Seebach D. Angew. Chem. 100:1988;1685-1715.
190. (b) Corey E.J., Imwinkelried R., Pikul S., Xiang Y.B. J. Am. Chem. Soc. 111:1989;5491-5493.
191. (c) Corey E.J., Imwinkelried R., Pikul S., Xiang Y.B. J. Am. Chem. Soc. 111:1989;5493-5495.
192. (d) Arnett E.M., Fisher F.J., Nichols M.A., Ribeiro A.A. J. Am. Chem. Soc. 111:1989;748-749.
193. (a) Wu Z., Zhang F., Danishefsky S.J. Angew. Chem. Int. Ed. Engl. 39:2000;4505-4508.
194. (b) Harris S.R., Kuduk S.D., Savin K., Balog A., Danishefsky S.J. Tetrahedron Lett. 40:1999;2263-2266.
195. (c) Harris S.R., Kuduk S.D., Balog A., Savin K.A., Danishefsky S.J. Tetrahedron Lett. 40:1999;2267-2270.
196. (d) Balog A., Harris S.R., Savin K., Zhang X.-G., Chou T.C., Danishefsky S.J. Angew. Chem. Int. Ed. Engl. 37:1998;2675-2678.
197. Sawada D., Shibazaki M. Angew. Chem. Int. Ed. Engl. 39:2000;209-213.
198. Bonner M.P., Thornton E.R. J. Am. Chem. Soc. 113:1991;1299-1308.
199. (a) Masamune S., Hirama M., Mori S., Ali S.A., Garvey D.S. J. Am. Chem. Soc. 103:1981;1568-1571.
200. (b) Masamune S., Choy W., Kerdesky F.A.J., Imperiali B. J. Am. Chem. Soc. 103:1981;1566-1568.
201. (c) Masamune S., Hirama M., Mori S., Ali S.A., Garvey D.S. J. Am. Chem. Soc. 103:1981;1568-1571.
202. Masamune S., Ali S.A., Snitman D.L., Garvey D.S. Angew. Chem. 92:1980;573-575.
203. Heathcock C.H., Pirrung M.C., Lampe J., Buse C.T., Young S.D. J. Org. Chem. 46:1981;2290-2300.
204. Hitchcock P.W., Starkmann R.A., Young D.W. Tetrahedron Lett. 42:2001;2381-2384.
205. Ziegler T., Lemanski G. Eur. J. Org.Chem. 1998;163-170.
206. Trost B.M., Florez J., Haller. J. Org. Chem. 53:1988;2394-2396.
207. Siegel C., Thornton E. Tetrahedron Lett. 27:1986;457-460.
208. (a) Evans D.A., Clark J.S., Metternich R., Novack V.J., Sheppard G.S. J. Am. Chem. Soc. 112:1990;866-868.
209. (b) Evans D.A., McGee L.R. J. Am. Chem. Soc. 103:1981;2876-2878.
210. (a) Mukaiyama T., Banno K., Narasaka K. J. Am. Chem. Soc. 96:1974;7503-7509.
211. (b) Mukaiyama T. Org. React. 28:1982;203-331.
212. Murata S., Suzuki M., Noyori R. Tetrahedron. 44:1988;4259-4279.
213. (a) Nakamura E., Yamago S., Machii D., Kuwajima I. Tetrahedron Lett. 29:1988;2207-2210
214. (b) Ando A., Miura T., Tatematsu T., Shioiri T. Tetrahedron Lett. 34:1993;1507-1510.
215. (a) Marshall J.A., Wang X.-j. J. Org. Chem. 56:1991;3211-3213.
216. (b) Tietze L.F., Schiemann K., Wegner C., Wulff C. Chem. Eur. J. 2:1996;1164-1172.
217. (a) Ishihara K., Miyata M., Hattori K., Tada T., Yamamoto H. J. Am. Chem. Soc. 116:1994;10520-10524.
218. (b) Hattori K., Miyata M., Yamamoto H. J. Am. Chem. Soc. 115:1993;1151-1152.
219. Gennari C., Colombo L., Bertolini G., Schimperna G. J. Org. Chem. 52:1987;2754-2760.
220. Gennari C., Gozzi P.G. J. Org. Chem. 53:1988;4015-4021.
221. Gennari C., Molinari F., Gozzi P.G., Oliva A. Tetrahedron Lett. 30:1989;5163-5166.
222. Evans D.A., Cage J.R. J. Org. Chem. 57:1992;1958-1961.
223. Evans D.A., Cage J.R. Tetrahedron Lett. 31:1990;6129-6132.
224. Ley S.V., Cox L.R., Worrall J.M. J. Chem. Soc. Perkin Trans. 1. 20:1998;3349-3354.
225. Furstner A. Synthesis. 1989;571-590.
226. Knochel P., Singer R.D. Chem. Rev. 93:1993;2117-2188.
227. Dewar M.J.S., Merz K.M. J. Am. Chem. Soc. 109:1987;6553-6554.
228. Maiz J., Arrieta A., Lopez X., Ugalde J.M., Cossio F.P. Tetrahedron Lett. 34:1993;6111-6114.
229. Mi A., Wang Z., Zhang J., Jiang Y. Synth. Commun. 27:1997;1469-1474.
230. Knochel P., Brieden W., Rozema M.J., Eisenberg C. Tetrahedron Lett. 34:1993;5881-5884.
231. Andres J.M., Martin Y., Pedrosa R., Perez-Encabo A. Tetrahedron. 53:1997;3787-3794.
232. Koert U., Wagner H., Pidun U. Chem. Ber. 127:1994;1447-1457.
233. Bodwell G.J., Davies S.G., Mortlock A.A. Tetrahedron. 47:1991;10077-10086.
234. Casiraghi G., Bigi F., Casnati G., Sartori G., Soncini P., Fava G.G., Belicchi F.M. J. Org. Chem. 53:1988;1779-1785.
235. Paterson I., Lister M.A. Tetrahedron Lett. 29:1988;585-588.
236. Paterson I., Lister M.A., McClure C.K. Tetrahedron Lett. 28:1987;1229-1232.
237. Paterson I., Lister M.A., McClure C.K. Tetrahedron Lett. 27:1986;4787-4790.
238. Paterson I., Goodman J.M., Lister M.A., Schumann R.C., McClure C.K., Norcross R.D. Tetrahedron. 46:1990;4663-4684.
239. Paterson I., Goodman J.M., Isaka M. Tetrahedron Lett. 30:1989;7121-7124.
240. Reetz M.T., Rivadeneira E., Niemeyer C. Tetrahedron Lett. 31:1990;3863-3866.
241. Yamamoto Y., Asao N. Chem. Rev. 93:1993;2207-2293.
242. Fleming I. Heathcock C.H. Comprehensive Organic Synthesis. Vol. 2:1991;595-628 Pergamon, Oxford.
243. Hoffmann R.W., Endesfelder A., Zeiss H.J. Carbohydr. Res. 123:1983;320-325.
244. Brown H.C., Bhat K.S. J. Am. Chem. Soc. 108:1986;5919-5923.
245. Brown H.C., Bhat K.S., Randad R.S. J. Org. Chem. 54:1989;1570-1576.
246. Yamamoto Y., Yamada J., Kadota I. Tetrahedron Lett. 32:1991;7069-7072.
247. (a) Yamamoto Y., Komatsu T., Maruyama K. J. Chem. Soc. Chem. Commun. 1985;814-816.
248. (b) Mikami K., Yoshida A. Tetrahedron Lett. 35:1994;7793-7796.
249. (c) Mikami K., Narisawa S., Shimizu M., Terada M. J. Am. Chem. Soc. 114:1992;6566-6568.
250. Roush W.R., Hoong L.K., Palmer M.A.J., Park J.C. J. Org. Chem. 55:1990;4109-4117.
251. Roush W.R., Adam M.A., Walts A.E., Harris D.J. J. Am. Chem. Soc. 108:1986;3422-3434.
252. (a) Roush W.R., Palkowitz A.D., Ando K. J. Am. Chem. Soc. 112:1990;6348-6359.
253. (b) Roush W.R., Halterman R.L. J. Am. Chem. Soc. 108:1986;294-296.
254. Coe J.W., Roush W.R. J. Org. Chem. 54:1989;915-930.
255. Roush W.R., Palkowitz A.D., Palmer M.A.J. J. Org. Chem. 52:1987;316-318.
256. Roush W.R., Walts A.E., Hoong L.K. J. Am. Chem. Soc. 107:1985;8186-8190.
257. Roush W.R., Brown B.B. J. Org. Chem. 58:1993;2151-2162.
258. Roush W.R., Brown B.B. J. Org. Chem. 58:1993;2162-2172.
259. Roush W.R., Brown B.B., Drozda S.E. Tetrahedron Lett. 29:1988;3541-3544.
260. (a) Roush W.R., Straub J.A., VanNieuwenhze M.S. J. Org. Chem. 56:1991;1636-1648.
261. (b) Roush W.R., Lin X., Straub J.A. J. Org. Chem. 56:1991;1649-1655.
262. Niel G., Roux F., Maisonnasse Y., Maugras I., Poncet J., Jouin P. J. Chem. Soc. Perkin Trans. 1. 1994;1275-1280.
263. Roush W.R., Grover P.T., Lin X. Tetrahedron Lett. 31:1990;7563-7566.
264. Roush W.R., Grover P.T. Tetrahedron Lett. 31:1990;7567-7570.
265. Akita H., Yamada H., Matsukura H., Nakata T., Oishi T. Tetrahedron Lett. 31:1990;1735-1738.
266. Roush W.R., Palkowitz A.D. J. Org. Chem. 54:1989;3009-3011.
267. Roush W.R., Banfi L. J. Am. Chem. Soc. 110:1988;3979-3982.
268. Hoffmann R.W., Dresely S., Hildebrandt B. Chem. Ber. 121:1988;2225-2230.
269. (a) Hoffmann R.W., Landmann B. Chem. Ber. 119:1986;2013-2024.
270. (b) Hoffmann R.W., Zeiss H.-J., Ladner W., Tabche S. Chem. Ber. 115:1982;2357-2370
271. (c) Herold T., Schrott U., Hoffmann R.W. Chem. Ber. 114:1981;359-374.
272. Hoffmann R.W., Dresely S. Tetrahedron Lett. 28:1987;5303-5306.
273. Hoffmann R.W., Weidmann U. Chem. Ber. 118:1985;3966-3979.
274. Brown H.C., Ramachandran P.V. Pure Appl. Chem. 63:1991;307.
275. Barett A.G.M., Seefeld M.A.K. J. Chem. Soc. Chem. Commun. 1993;339-341.
276. Wang Z., Deschênes D. J. Am. Chem. Soc. 114:1992;1090-1091.
277. Brown H.C., Jadhav P.K. J. Am. Chem. Soc. 105:1983;2092-2093.
278. Brown H.C., Bhat K.S., Randad R.S. J. Org. Chem. 52:1987;319-320.
279. Brown H.C., Bhat K.S., Randad R.S. J. Org. Chem. 52:1987;3701-3702.
280. (a) Barrett A.G.M., Edmunds J.J., Hendrix J.A., Malecha J., Parkinson C.J. J. Chem. Soc. Chem. Commun. 1992;1240-1242
281. (b) Barrett A.G.M., Edmunds J.J., Hendrix J.A., Horita K., Parkinson C.J. J. Chem. Soc. Chem. Commun. 1992;1238-1240.
282. Brown H.C., Dhar R.K., Bakshi R.K., Pandiarajan P.K., Singaram B. J. Am. Chem. Soc. 111:1989;3441-3442.
283. Garcia J., Kim B.M., Masamune S. J. Org. Chem. 52:1987;4831-4832.
284. Short R.P., Masamune S. J. Am. Chem. Soc. 111:1989;1892-1894.
285. (a) Roush W.R., Grover P.T. Tetrahedron Lett. 31:1990;7567-7570
286. (b) Roush W.R., Grover P.T. Tetrahedron Lett. 48:1992;1981-1998.
287. Panek J.S., Schaus J.V. Tetrahedron. 53:1997;10971-10982.
288. Akita H., Yamada H., Matsukura H., Nakata T., Oishi T. Tetrahedron Lett. 31:1990;1735-1738.
289. (a) Marshall J.A., Luke G.P. J. Org. Chem. 56:1991;483-485.
290. (b) Marshall J.A., Gung W.Y. Tetrahedron Lett. 29:1988;1657-1660.
291. (c) Marshall J.A., Gung W.Y. Tetrahedron Lett. 29:1988;3899-3902.
292. (d) Marshall J.A., Markwalder J.A. Tetrahedron Lett. 29:1988;4811-4814.
293. Nakata T., Schmid G., Vranesic B., Okigawa M., Smith-Palmer T., Kishi Y. J. Am. Chem. Soc. 100:1978;2933-2935.
294. Fukuyama T., Akasaka K., Karanewsky D.S., Wang C.-L.J., Schmid G., Kishi Y. J. Am. Chem. Soc. 101:1979;262-263.
295. Hoffmann R.W. Angew. Chem. 99:1987;503-517.
296. Beckett R.P., Davies S.G., Mortlock A.A. Tetrahedron: Asymmetry. 3:1992;123-136.
297. Burgess K., Henderson I. Tetrahedron Lett. 31:1990;6949-6952.
298. Burgess K., Chaplin D.A. Tetrahedron Lett. 33:1992;6077-6080.
299. Osida J., Okamoto M., Azuma S., Tanaka T. Tetrahedron: Asymmetry. 8:1997;2579-2584.
300. Polniaszek R.P., Bell S.J. Tetrahedron Lett. 37:1996;575-578.
301. Depezay J.-C., Dureault A., Prange T. Tetrahedron Lett. 25:1984;1459-1462.
302. Roush W.R., Palkowitz A.D. J. Am. Chem. Soc. 109:1987;953-955.
303. Ireland R.E., Wipf P., Roper T. J. Org. Chem. 55:1990;2284-2285.
304. Panek J.S., Beresis R. J. Org. Chem. 58:1993;809-811.
305. Ditrich K., Bube T., Stuermer R., Hoffmann R.W. Angew. Chem. Int. Ed. Engl. 25:1986;1016-1018.
306. Carruthers W. Cycloaddition Reactions in Organic Synthesis. 1990;Pergamon, Oxford.
307. Cardona F., Valenza S., Goti A., Brandi A. Eur. J. Org. Chem. 1999;1319-1324.
308. Borrachero P., Cabrera F., Dianez M.J., Estrada M.D., Gomez-Guillena M., Lopez-Castro A., Moreno J.M., de Paza J.L., Perez-Garrido S. Tetrahedron: Asymmetry. 10:1999;77-98.
309. Valenza S., Cordero F.M., Brandi A., Guidi A., Altamura M., Giolitti A., Giuntini F., Pasqui F., Renzetti A.R., Maggi C.A. J. Org. Chem. 65:2000;4003-4008.
310. Mzengeza S., Whitney R.A. J. Org. Chem. 53:1988;4074-4081.
311. Brandi A., Cicchi S., Goti A., Pietrusiewicz K.M. Tetrahedron: Asymmetry. 2:1991;1063-1074.
312. Goti A., Cicchi S., Brandi A., Pietrusiewicz K.M. Tetrahedron: Asymmetry. 2:1991;1371-1378.
313. Brandi A., Cicchi S., Goti A., Pietrusiewicz K.M. Phosphorus, Sulphur, Silicon and Relat. Elem. 75:1993;155-158.
314. Shing T.K.M., Zhong Y.-L., Mak T.C.W., Wang Eu.-ji., Xue F. J. Org. Chem. 63:1998;414-415.
315. Molander G.A., McWilliams J.C., Noll B.C. J. Am. Chem. Soc. 119:1997;1265-1276.
316. Fray A.H., Meyers A.I. J. Org. Chem. 61:1996;3362-3374.
317. Dirat O., Kouklovsky C., Longlois Y., Lesot P., Courtieu J. Tetrahedron: Asymmetry. 10:1999;3197-3207.
318. Kim H.R., Kim H.J., Duffy J.L., Olmstead M.M., Ruhlandt-Senge K., Kurth M.J. Tetrahedron Lett. 32:1991;4259-4262.
319. Hashimoto S.-ichi., Watanabe N., Kawano K., Ikegami S. Synth. Commun. 24:1994;3277-3288.
320. Bartels A., Jones P.G., Liebscher J. Synthesis. 1998;1645-1654.
321. Podlech J., Steurer S. Synthesis. 1999;650-654.
322. Ishibashi H., Kameoka C., Kodama K., Ikeda M. Synlett. 1995;915-917.
323. He M., Tanimori S., Ohira S., Nakayama M. Tetrahedron. 53:1997;13307-13314.
324. Paquette L.A., Keith S.L., Romine J.L. Tetrahedron. 43:1987;4989-5002.
325. Togni A., Pastor S.D., Rihs G. Helv. Chim. Acta. 72:1989;1038-1042.
326. Togni A., Pastor S.D. Helv. Chim. Acta. 72:1989;1471-1478.
327. Coxon J.M., Froeze R.D.J., Ganguly B., Marchand A.P., Morokuma K. Synlett. 1999;1681-1703.
328. Waldmann H. Synthesis. 1994;535-551.
329. Defoin A., Pires J., Tissot I., Tschamber T., Bur D., Sehnder M., Streith J. Tetrahedron: Asymmetry. 2:1991;1209-1221.
330. Paquette L.A. Morrison J.D. Asymmetric Synthesis. Vol. 3:1984;455-503 Academic, New York.
331. Tolbert L.M., Alim B. J. Am. Chem. Soc. 106:1984;3806-3810.
332. Hattori K., Yamamoto H. J. Org. Chem. 57:1992;3264-3265.
333. Hattori K., Yamamoto H. Tetrahedron. 49:1993;1749-1760.
334. Bailey P.D., Londesbrough D.J., Hancox T.C., Heffernan J.D., Holmes A.B. J. Chem. Soc. Chem. Commun. 1994;2543-2544.
335. Danishefsky S.J., DeNinno M.P. Angew. Chem. 99:1987;15-23.
336. Bednarski M.D., Lyssikatos J.P. Fleming L. Comprehensive Organic Synthesis. Vol. 2:1991;661 Pergamon, Oxford.
337. Bednarski M., Danishefsky S. J. Am. Chem. Soc. 105:1983;6968-6969.
338. Bednarski M., Danishefsky S. J. Am. Chem. Soc. 108:1986;7060-7067.
339. Gouverneur V., Dive G., Ghosez L. Tetrahedron: Asymmetry. 2:1991;1173-1176.
340. Martin S.F., Hartmann M., Josey J.A. Tetrahedron Lett. 33:1992;3583-3586.
341. Gouverneur V., Ghosez L. Tetrahedron: Asymmetry. 1:1990;363-366.
342. David S., Lubineau A., Vatele J.-M.J. Chem. Soc. Chem. Commun. 1978;535-536.
343. David S., Eustache J., Lubineau A. J. Chem. Soc. Perkin Trans. 1. 1979;1795-1798.
344. David S., Eustache J. J. Chem. Soc. Perkin Trans. 1. 1979;2230-2234.
345. Jurczak J., Golebiowski A. Chem. Rev. 89:1989;149-164.
346. Danishefsky S.J., Armistead D.M., Wincott F.E., Selnick H.G., Hungate R. J. Am. Chem. Soc. 109:1987;8117-8119.
347. Golebiowski A., Jurczak J. Synlett. 1993;241-245.
348. Golebiowski A., Jacobsson U., Raczko J., Jurczak J. J. Org. Chem. 54:1989;3759-3760.
349. Midland M.M., Graham R.S. J. Am. Chem. Soc. 106:1984;4294-4296.
350. Togni A. Organometallics. 9:1990;3106-3113.
351. Posner G.H., Carry J.-C., Anjeh T.E.N., French A.N. J. Org. Chem. 57:1992;7012-7014.
352. Herzog H., Koch H., Scharf H.-D., Runsink J. Chem. Ber. 120:1987;1737-1740.
353. Herzog H., Koch H., Runsink J., Scharf H.-D. Tetrahedron. 42:1986;3547-3558.
354. Kolodiazhnyi O.I., Sheiko S.Y. Russ. J. Gen. Chem. (Zh. Obshch. Khim.). 71:2001;977-978.
355. Kolodiazhnyi O.I. Tetrahedron: Asymmetry. 9:1998;1279-1332.
356. Kolodiazhnyi O.I. Phosphorus, Sulphur, Silicon Relat. Elem. 177:2002;2111-2114.
357. Kolodiazhnyi O.I., Sheiko S.Y., Guliaiko I.V., Gryshkun E.V. Phosphorus, Sulphur, Silicon Relat. Elem. 177:2002;2269-2270.
358. Yamagishi T., Suemune K., Yokomatsu T., Shibuya S. Tetrahedron Lett. 42:2001;5033-5036.
359. Yamagishi T., Suemune K., Yokomatsu T., Shibuya S. Tetrahedron. 58:2002;2577-2583.
360. Yamagishi T., Suemune K., Yokomatsu T., Shibuya S. Synlett. 2002;1471-1474.
361. Hirama M., Hioki H., Ito S., Kabuto C. Tetrahedron Lett. 29:1988;3121-3124.
362. Komatsu N., Murakami T., Nishibayashi Y., Sugita T., Uemura S. J. Org. Chem. 58:1993;3697-3702.
363. Fujita K.-i., Iwaoka M., Tomoda S. Chem. Lett. 1992;1123-1124.
364. Ruano Garcia J.L., Alcudia A., Prado M., Barros D., Maestro M.C., Fernandez I. J. Org. Chem. 65:2000;2856-2862.
365. Annunziata R., Cozzi F., Cinquini M. J. Chem. Soc. Perkin Trans. 1. 1985;251-254.
366. Annunziata R., Cinquini M., Cozzi F., Gilardi A., Cardani S., Poll G., Scolastico C. J. Chem. Soc. Perkin Trans. 1. 1985;255-259.
367. Kolodiazhnyi O.I., Grishkun E.V. Phosphorus, Sulphur, Silicon Relat. Elem. 115:1996;115-124.
368. Kolodiazhnyi O.I., Grishkun E.V. Tetrahedron: Asymmetry. 7:1996;967-970.
369. Barett A.G.M., Malecha J.W. J. Org. Chem. 56:1991;5243-5245.
370. Barett A.G.M., Seefeld M.A. Tetrahedron. 49:1993;7857-7870.
371. Trost B.M., Mallart S. Tetrahedron Lett. 34:1993;8025-8028.
372. Kolodiazhnyi O.I., Sheiko S.Y., Grishkun E.V. Heteroatom. Chem. 11:2000;138-143.