Stereocontrol in radical Mannich equivalents for aminosugar synthesis: haloacetal and 2-(phenylthio)vinyl tethered radical additions to α-hydroxyhydrazones

Tetrahedron

Volumn 64, Issue 51, 2008, Pages 11549-11557

  Friestad, Gregory K ^a   Jiang, Tao ^a   Fioroni, Gina M ^a  

^a E11 SSH   (United States)

Author keywords

Aminosugars; Hydrazones; Radical cyclization; Stereoselectivity

Indexed keywords

ACETAL DERIVATIVE; AMINOSUGAR; CARBON; FLUORIDE; HYDRAZONE DERIVATIVE; NITROGEN; SILICON; THIOPHENOL; VINYL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MANNICH REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 55549123832     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.013     Document Type: Article

References (172)

1. Reviews:
2. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069-1094
3. Bloch R. Chem. Rev. 98 (1998) 1407-1438
4. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895-1946
5. Denmark S.E., and Nicaise O.J.-C. Chem. Commun. (1996) 999-1004
6. Yamada K.-I., and Tomioka K. Chem. Rev. 108 (2008) 2874-2886
7. Reviews:
8. Friestad G.K., and Mathies A.K. Tetrahedron 63 (2007) 2541-2569
9. Vilaivan T., Bhanthumnavin W., and Sritana-Anant Y. Curr. Org. Chem. 9 (2005) 1315-1392
10. Reviews of radical reactions and their stereocontrol:
11. In: Renaud P., and Sibi M. (Eds). Radicals in Organic Synthesis (2001), Wiley-VCH, New York, NY
12. Curran D.P., Porter N.A., and Giese B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications (1995), VCH, New York, NY
13. Sibi M.P., and Porter N.A. Acc. Chem. Res. 32 (1999) 163-171
14. Renaud P., and Gerster M. Angew. Chem., Int. Ed. 37 (1998) 2563-2579
15. Reviews of radical additions to imines and related acceptors:
16. Friestad G.K. Tetrahedron 57 (2001) 5461-5496
17. Fallis A.G., and Brinza I.M. Tetrahedron 53 (1997) 17543-17594
18. Stork G., and Dowd S.R. J. Am. Chem. Soc. 85 (1963) 2178-2180
19. Wittig G., Frommeld H.D., and Suchanek P. Angew. Chem., Int. Ed. Engl. 2 (1963) 683
20. Even less basic organocerium reagents can promote aza-enolization of hydrazones:. Enders D., Diez E., Fernandez R., Martin-Zamora E., Munoz J.M., Pappalardo R.R., and Lassaletta J.M. J. Org. Chem. 64 (1999) 6329-6336
21. Friestad G.K., and Qin J. J. Am. Chem. Soc. 122 (2000) 8329-8330
22. Friestad G.K., and Qin J. J. Am. Chem. Soc. 123 (2001) 9922-9923
23. Friestad G.K., Shen Y., and Ruggles E.L. Angew. Chem., Int. Ed. 42 (2003) 5061-5063
24. Friestad G.K., Draghici C., Soukri M., and Qin J. J. Org. Chem. 70 (2005) 6330-6338
25. Friestad G.K., Qin J., Suh Y., and Marié J.-C. J. Org. Chem. 71 (2006) 7016-7027
26. Korapala C.S., Qin J., and Friestad G.K. Org. Lett. 9 (2007) 4246-4249
27. Friestad G.K., and Ji A. Org. Lett. 10 (2008) 2311-2313
28. Miyabe H., Ushiro C., and Naito T. Chem. Commun. (1997) 1789-1790
29. Miyabe H., Fujii K., and Naito T. Org. Lett. 1 (1999) 569-572
30. Miyabe H., Ushiro C., Ueda M., Yamakawa K., and Naito T. J. Org. Chem. 65 (2000) 176-185
31. Ueda M., Miyabe H., Teramachi M., Miyata O., and Naito T. Chem. Commun. (2003) 426-427
32. Ueda M., Miyabe H., Teramachi M., Miyata O., and Naito T. J. Org. Chem. 70 (2005) 6653-6660
33. Ueda M., Ono A., Nakao D., Miyata O., and Naito T. Tetrahedron Lett. 48 (2007) 841-844
34. Miyata O., Takahashi S., Tamura A., Ueda M., and Naito T. Tetrahedron 64 (2008) 1270-1284
35. Bertrand M.P., Feray L., Nouguier R., and Stella L. Synlett (1998) 780-782
36. Bertrand M.P., Feray L., Nouguier R., and Perfetti P. Synlett (1999) 1148-1150
37. Bertrand M.P., Coantic S., Feray L., Nouguier R., and Perfetti P. Tetrahedron 56 (2000) 3951-3961
38. Bertrand M., Feray L., and Gastaldi S. C. R. Chimie 5 (2002) 623-638
39. For other selected approaches to intermolecular radical addition to C{double bond, long}N bonds, see:
40. Halland N., and Jørgensen K.A. J. Chem. Soc., Perkin Trans. 1 (2001) 1290-1295
41. Fernández M., and Alonso R. Org. Lett. 5 (2003) 2461-2464
42. Zhang Z., Wang G.-W., Miao C.-B., Dong Y.-W., and Shen Y.-B. Chem. Commun. (2004) 1832-1833
43. Miyabe H., Yamaoka Y., and Takemoto Y. J. Org. Chem. 70 (2005) 3324-3327
44. Yamada K., Yamamoto Y., Maekawa M., Akindele T., Umeki H., and Tomioka K. Org. Lett. 8 (2006) 5729-5732
45. Cho D.H., and Jang D.O. Chem. Commun. (2006) 5045-5047
46. Godineau E., and Landais Y. J. Am. Chem. Soc. 19 (2007) 12662-12663
47. Nishiyama H., Kitajima T., Matsumoto M., and Itoh K. J. Org. Chem. 49 (1984) 2298-2300
48. Stork G., and Kahn M. J. Am. Chem. Soc. 107 (1985) 500-501
49. Reviews of silicon tethered reactions:
50. Gauthier Jr. D.R., Zandi K.S., and Shea K.J. Tetrahedron 54 (1998) 2289-2338
51. Fensterbank L., Malacria M., and Sieburth S.M. Synthesis (1997) 813-854
52. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063-2192
53. Bols M., and Skrydstrup T. Chem. Rev. 95 (1995) 1253-1277
54. Friestad G.K. Org. Lett. 1 (1999) 1499-1501
55. Friestad G.K., and Massari S.E. Org. Lett. 2 (2000) 4237-4240
56. Friestad G.K., and Massari S.E. J. Org. Chem. 69 (2004) 863-875
57. Friestad G.K., Jiang T., and Fioroni G.M. Tetrahedron: Asymmetry 14 (2003) 2853-2856
58. For other radical equivalents to Mannich-type reactions, see:
59. Miyabe H., Fujii K., Goto T., and Naito T. Org. Lett. 2 (2000) 4071-4074
60. Inokuchi T., and Kawafuchi H. Synlett (2001) 421-423
61. Clerici A., Cannella R., Pastori N., Panzeri W., and Porta O. Tetrahedron 62 (2006) 5986-5994
62. For a review, see:. Kolter T., and Sandhoff K. Angew. Chem., Int. Ed. 38 (1999) 1532-1568
63. Reviews:
64. Heightman T.D., and Vasella A.T. Angew. Chem., Int. Ed. 38 (1999) 750-770
65. In: Chapleur Y. (Ed). Carbohydrate Mimics (1998), Wiley-VCH, Weinheim
66. Nash R.J., Watson A.A., and Asano N. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives (1996), Pergamon, Tarrytown, NY 345-376
67. Review:. Hauser F.M., and Ellenberger S.R. Chem. Rev. 86 (1986) 35-67
68. Friestad G.K., and Fioroni G.M. Org. Lett. 7 (2005) 2393-2396
69. For the first such approach, see:
70. Acton E.M., Tong G.L., Mosher C.W., and Wolgemuth R.L. J. Med. Chem. 27 (1984) 638-645
71. For more recent studies:
72. Zhang G., Fang L., Zhu L., Aimiuwu J.E., Shen J., Cheng H., Muller M.T., Lee G.E., Sun D., and Wang P.G. J. Med. Chem. 48 (2005) 5269-5278
73. Jeffrey S.C., Nguyen M.T., Andreyka J.B., Meyer D.L., Doronina S.O., and Senter P.D. Bioorg. Med. Chem. Lett. 16 (2006) 358-362
74. Ciesielska E., Studzian K., Wasowska M., Oszczapowicz I., and Szmigiero L. Cell Biol. Toxicol. 21 (2005) 139-147
75. Portugal J., Cashman D.J., Trent J.O., Ferrer-Miralles N., Przewloka T., Fokt I., Priebe W., and Chaires J.B. J. Med. Chem. 48 (2005) 8209-8219
76. For recent approaches, see:
77. Friestad G.K., Jiang T., and Mathies A.K. Org. Lett. 9 (2007) 777-780
78. Mendlik M.T., Tao P., Hadad C.M., Coleman R.S., and Lowary T.L. J. Org. Chem. 71 (2006) 8059-8070
79. Parker K.A., and Chang W. Org. Lett. 7 (2005) 1785-1788
80. Trost B.M., Jiang C.H., and Hammer K. Synthesis (2005) 3335-3345
81. Parker K.A., and Chang W. Org. Lett. 5 (2003) 3891-3893
82. Avenoza A., Busto J.H., Corzana F., Peregrina J.M., Sucunza D., and Zurbano M.M. Tetrahedron: Asymmetry 14 (2003) 1037-1043
83. Ginesta X., Pasto M., Pericas M.A., and Riera A. Org. Lett. 17 (2003) 3001-3004
84. Cutchins W.W., and McDonald F.E. Org. Lett. 4 (2002) 749-752
85. Liberek B., Dabrowska A., Frankowski R., Matuszewska M., and Smiatacz Z. Carbohydr. Res. 337 (2002) 1803-1810
86. Davies S.G., Smyth G.D., and Chippindale A.M. J. Chem. Soc., Perkin Trans. 1 (1999) 3089-3104
87. Szechner B., Achmatowicz O., and Badowska-Roslonek K. Pol. J. Chem. 73 (1999) 1133-1141
88. Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., and Koumbis A.E. Chem.-Eur. J. 5 (1999) 2648-2667
89. Daley L., Roger P., and Monneret C. J. Carbohydr. Chem. 16 (1997) 25-48
90. Wade P.A., D'Ambrosio S.G., Rao J.A., Shah-Patel S., Cole D.T., Murray Jr. J.K., and Carroll P.J. J. Org. Chem. 62 (1997) 3671-3677
91. Sibi M., Lu J., and Edwards J. J. Org. Chem. 62 (1997) 5864-5872 Sibi et al. (Ref. 21o) provide an extensive list of reference to earlier syntheses
92. DeShong P., Dicken C.M., Leginus J.M., and Whittle R.R. J. Am. Chem. Soc. 106 (1984) 5598-5602
93. Xu Z., Johannes C.W., La D.S., Hofilena G.E., and Hoveyda A.H. Tetrahedron 53 (1997) 16377-16390
94. Mukaiyama T., Goto Y., and Shoda S. Chem. Lett. (1983) 671-674
95. Fuganti C., Grasselli P., and Pedrocchi-Fantoni G. J. Org. Chem. 48 (1983) 910-912
96. Kita Y., Itoh F., Tamura O., Ke Y.Y., Miki T., and Tamura Y. Chem. Pharm. Bull. 37 (1989) 1446-1451
97. Po S.-Y., and Uang B.-J. Tetrahedron: Asymmetry 5 (1994) 1869-1872
98. See Ref. 42.
99. Ueno Y., Chino K., Watanabe M., Moriya O., and Okawara M. J. Am. Chem. Soc. 104 (1982) 5564-5566
100. Stork G., Mook R., Biller S., and Rychnovsky S.D. J. Am. Chem. Soc. 105 (1983) 3741-3742
101. Stork G. Bull. Soc. Chim. Fr. 127 (1990) 675-680
102. Stork G., and Ouerfelli O. New J. Chem. 16 (1992) 95-98
103. For a comprehensive review, see:
104. Salom-Roig X.J., Dénès F., and Renaud P. Synthesis (2004) 1903-1928
105. For more recent examples, see:
106. Yoshimitsu T., Sasaki S., Arano Y., and Nagaoka H. J. Org. Chem. 69 (2004) 9262-9268
107. Ward D.E., Gai Y.Z., Qiao Q., and Shen J.H. Can. J. Chem. 82 (2004) 254-267
108. Itoh T., Kudo K., Yokota K., Tanaka N., Hayase S., and Renou M. Eur. J. Org. Chem. (2004) 406-412
109. Clive D.L.J., Yu M.L., and Sannigrahi M. J. Org. Chem. 69 (2004) 4116-4125
110. Yadav J.S., and Srihari P. Tetrahedron: Asymmetry 15 (2004) 81-89
111. Noya B., Paredes M.D., Ozores L., and Alonso R. J. Org. Chem. 65 (2000) 5960-5968
112. Renaud P., and Villar F. Tetrahedron Lett. 39 (1998) 8655-8658
113. Renaud P., Villar F., Kolly-Kovac T., and Equey O. Chem.-Eur. J. 9 (2003) 1566-1577
114. Renaud P., Corminboeuf O., and Schiesser C.H. Chem.-Eur. J. 9 (2003) 1578-1584
115. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
116. David S., and Hanessian S. Tetrahedron 41 (1985) 643-663
117. Blunden S.J., Cusack P.A., and Smith P.J. J. Organomet. Chem. 325 (1987) 141-152
118. Alais J., and Veyrieres A. J. Chem. Soc., Perkin Trans. 1 (1981) 377-381
119. For detailed conformational analysis and NMR data of daunosamine derivatives and their diastereomers, see. Fronza G., Fuganti C., and Grasselli P. J. Chem. Soc., Perkin Trans. 1 (1982) 885-891
120. For a review of 3-epi-daunosamine derivatives, see Ref. 17;
121. For prior syntheses see Ref. 21g, and the following:
122. Suami T., Tadano K., Suga A., and Ueno Y. J. Carbohydr. Chem. 3 (1984) 429-441
123. Danishefsky S.J., and Maring C.J. J. Am. Chem. Soc. 107 (1985) 1269-1274
124. Herczegh P., Zsély M., Kovács I., Batta G., and Sztaricskai F.J. Tetrahedron Lett. 31 (1990) 1195-1198
125. 2 spin systems with A and B at δ 1.5-2.2 with geminal coupling, characteristic of the C2 position of 2-deoxyglycosides. Furthermore, satisfactory combustion analysis was obtained on the diastereomer mixture.
126. Beckwith A.L.J., and Schiesser C.H. Tetrahedron 41 (1985) 3925-3941
127. Spellmeyer D.C., and Houk K.N. J. Org. Chem. 52 (1987) 959-974
128. Deslongchamps P. Stereoelectronic Effects in Organic Chemistry (1983), Pergamon, New York, NY
129. Although a 1,3-allylic strain model may also be considered, the C{double bond, long}N of the (E)-hydrazone bears no cis-substituent, so such an effect is expected to be minimal.
130. Similar vicinal dipole repulsion has been observed previously:. Friestad G.K., and Mathies A.K. Tetrahedron 63 (2007) 9373-9381
131. Reviews:
132. Miyata O., and Naito T. C. R. Chimie 4 (2001) 401-421
133. Naito T. Heterocycles 50 (1999) 505-541
134. For selected recent examples, see:
135. Miyata O., Nakajima E., and Naito T. Chem. Pharm. Bull. 49 (2001) 213-224
136. Miyata O., Muroya K., Kobayashi T., Yamanaka R., Kajisa S., Koide J., and Naito T. Tetrahedron 58 (2002) 4459-4479
137. Miyata O., Kajisa S., Ueda M., Yamauchi M., and Naito T. Chem. Pharm. Bull. 53 (2005) 995-1002
138. Fernández-Gonzalez M., and Alonso R. J. Org. Chem. 71 (2006) 6767-6775
139. Alkynylsilanes have not been employed as silicon-tethered radical precursors, though their use as acceptors is known, see:
140. Stork G., Suh H.S., and Kim G. J. Am. Chem. Soc. 113 (1991) 7054-7056
141. Mazeas D., Skrydstrup T., Doumeix O., and Beau J.-M. Angew. Chem., Int. Ed. Engl. 33 (1994) 1383-1386
142. Xi Z., Rong J., and Chattopadhyaya J. Tetrahedron 50 (1994) 5255-5272
143. Garg N., Hossain N., and Chattopadhyaya J. Tetrahedron 50 (1994) 5273-5278
144. Sukeda M., Ichikawa S., Matsuda A., and Shuto S. J. Org. Chem. 68 (2003) 3465-3475
145. This manuscript provides experimental details for 2-(phenylthio)vinyl addition, which were not previously published. For discussion, including details regarding variable E/Z ratios, see the original communication (Ref. 13).
146. Barton T.J., Lin J., Ijadi-Maghsoodi S., Power M.D., Zhang X., Ma Z., Shimizu H., and Gordon M.S. J. Am. Chem. Soc. 117 (1995) 11695-11703
147. Matsumoto H., Kato T., Matsubara I., Hoshino Y., and Nagai Y. Chem. Lett. (1979) 1287-1290
148. For stereochemical assignment of 9d″, see Ref. 12.
149. For representative methods, see:
150. 4:. Autrey R.L., and Scullard P.W. J. Am. Chem. Soc. 90 (1968) 4924-4929
151. Satoh T., Taguchi D., Suzuki C., and Fujisawa S. Tetrahedron 57 (2001) 493-500
152. 2:. Corey E.J., and Shulman J.I. J. Org. Chem. 35 (1970) 777-780
153. Hewson A.T., and MacPherson D.T. J. Chem. Soc., Perkin Trans. 1 (1985) 2625-2636
154. 4:. Mukaiyama T., Kamio K., Kobayashi S., and Takei M. Bull. Chem. Soc. Jpn. 45 (1972) 3723
155. Pariza R.J., and Fuchs P.L. J. Org. Chem. 50 (1985) 4252-4266
156. Wilson S.R., Georgiadis G.M., Khatri H.N., and Bartmess J.E. J. Am. Chem. Soc. 102 (1980) 3577-3583
157. 2:. Mura Jr. A.J., Majetich G., Grieco P.A., and Cohen T. Tetrahedron Lett. 16 (1975) 4437-4440
158. 2H:. Grayson J.I., and Warren S. J. Chem. Soc., Perkin Trans. 1 (1977) 2263-2272
159. HCl:. Pearson W.H., Bergmeier S.C., and Williams J.P. J. Org. Chem. 57 (1992) 3977-3987
160. 3-clay ('clayfen'):. Almqvist F., Ekman N., and Frejd T. J. Org. Chem. 61 (1996) 3794-3798
161. Hatanaka M., and Ueda I. Chem. Lett. (1991) 61-64
162. Syringe pump addition of the thiol was not required in this case. Addition of AIBN in four 0.2 equiv batches was required to ensure complete conversion.
163. Pearson has observed a similar inhibition by neighboring basic nitrogen. See Ref. 41f.
164. Ding H., and Friestad G.K. Org. Lett. 6 (2004) 637-640
165. Grieco P.A., and Dai Y. Tetrahedron Lett. 39 (1998) 6997-7000
166. 3CN).
167. Kimura Y., Matsumoto T., Suzuki M., and Terashima S. Bull. Chem. Soc. Jpn. 59 (1986) 663-664
168. Shelton C.J., and Harding M.M. J. Chem. Res., Synop. (1995) 158
169. Shelton C.J., and Harding M.M. J. Chem. Res., Miniprint (1995) 1201-1209 We thank Dr. M. Harding for kindly providing copies of the data
170. Aucagne V., Tatibouët A., and Rollin P. Tetrahedron 60 (2004) 1817-1826
171. For a detailed comparison of various daunosamine syntheses, see Supplementary data of Ref. 21a.
172. El Khadem H.S., and Matsuura D. Carbohydr. Res. 99 (1982) 143-156