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Original Articles

REAGENT-CONTROLLED ASYMMETRIC DIELS-ALDER REACTIONS. A REVIEW

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Pages 129-158 | Received 30 Nov 1992, Published online: 18 Feb 2009

References

  • Carruthers , W. 1990 . “Cycloaddition Reactions in Organic Synthesis” , 1 – 234 . New York : Pergamon Press . b) G. Desimoni, G. Tacconi, A. Barco and G. P. Pollini, “Natural Product Synthesis Through Pericyclic Reactions”, Chapter 5, p. 119, ACS Monograph 180: ACS, Washington D. C., 1983. c) F. Fringuelli and A. Taticchi, “Dienes in the Diels-Alder Reaction”, p. 1–343, John Wiley & Sons, New York, 1990. d) B. M. Trost, I. Fleming and L. A. Paquette, “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry”, Vol 5, Chapter 4.1, p. 315, Pergamon Press, New York, 1991
  • Trost , B. M. , Fleming , I. and Paquette , L. A. 1991 . “ Chapter 4.4 ” . In “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry” , Vol 5 , 513 New York : Pergamon Press . b) E. Ciganek, Org. React. 32, 1(1984). c) D. Craig, Chem. Soc. Rev., 16, 187(1987). d) R. L. Funk and K. P. C. Vollhardt, ibid., 9, 41(1980). e) D. F. Taber, “Intramolecular Diels-Alder and Alder Ene Reactions”, p. 1–60, Springer-Verlag, New York, 1984. f) G. Brieger and J. N. Bennett, Chem. Rev., 80, 63(1980). g) W. Oppolzer, Angew. Chem. Int. Ed. Engl., 16, 10(1977). h) W. Oppolzer, Synthesis, 798(1978). i) A. G. Fallis, Can. J. Chem. 62, 183(1984)
  • Boger , D. L. and Weinreb , S. M. 1987 . “Hetero Diels-Alder Methodology in Organic Synthesis” , 1 – 366 . New York : Academic Press . b) T. Kametani and S. Hibino, Advances in Heterocyclic Chemistry 42, 245(1987). c) D. Boger, Tetrahedron, 39, 2869(1983). d) S. M. Weinreb and J. I. Levin, Heterocycles, 12, 949(1979). e) D. L. Boger, Chem. Rev., 86, 781(1986). f) D. M. Stout and A. I. Meyers, ibid., 82, 223(1982). g) S. B. Needleman and M. C. C. Kuo, Chem. Rev., 62, 405(1962). h) B. M. Trost, I. Fleming and L. A. Paquette, “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modem Organic Chemistry”, p. 401, Vol 5, Chapter 4.2, Pergamon Press, New York, 1991. i) B. M. Trost, I, Fleming and L. A. Paquette, “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry”, p. 451, Vol 5, Chapter 4.3, Pergamon Press, New York, 1991
  • Evans , D. A. , Chapman , K. T. and Bisaha , J. 1988 . J. Am. Chem. Soc. , 110 : 1238 b) W. Oppolzer, Angew. Chem. Int. Ed. Engl., 23, 876(1984). c) Scheffold, R., “Modern Synthetic Methods 1986, p. 261, Springer Verlag, New York, 1986. d) J. W. ApSimon and T. L. Collier, Tetrahedron, 42, 5157(1986). e) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, and H.-U. Reissig, “Organic Synthesis Highlights, p. 54, VCH, New York, 1991. f) J. D. Morrison, “Asymmetric Synthesis”, p. 455, Chapter 7, Academic Press, New York, 1984.
  • Masamune , S. , Choy , W. , Peterson , J. S. and Sita , L. R. 1985 . Angew. Chem. Int. Ed. Engl. , 24 : 1 For the concept of double asymmetric synthesis strategy in the Diels-Alder reaction, see
  • Mulzer , J. , Altenbach , H. J. , Braun , M. , Krohn , K. and Reissig , H. U. 1991 . “Organic Synthesis Highlights” , 66 New York : VCH . For other reviews in this area, see:b) D. A. Evans, Science 240, 420(1988). c) H.-J. Altenbach, Nachr. Chem. Tech. Lab., 36, 906(1988). d) D. Schinzer, “Selectivities in Lewis Acid Promoted Reactions”, p. 281, Chapter 15, Kluwer Academic, Boston, 1988. e) E. J. Corey, Pure & Appl. Chem., 62, 1209(1990). f) K. Tomioka, Synthesis, 541(1990). g) K. Narasaka, ibid., 1(1991). h) G. Molander, Chem. Rev., 92, 29(1992). i) R. Scheffold, “Modern Synthetic Methods” 1989, p. 115, Springer Verlag, New York, 1989. j) H. B. Kagan and O. Riant, Chem. Rev., 92, 1007(1992). k) B. B. Lohray and V. Bhushan, Angew. Chem. Int. Ed. Engl., 31, 729, (1992). l) U. Pindur, G. Lutz, and C. Otto, ibid., 93, 741, (1993). m) L. Deloux and M. Srebnik, Chem. Rev., 93, 763(1993). n) For asymmetric Diels-Alder reaction catalyzed by chiral bases, see: O. Riant and H. B. Kagan, Tetrahedron Lett., 30, 7403(1989)
  • Hashimoto , S. I. , Komeshima , N. and Koga , K. 1979 . Chem. Commun. , : 437
  • Kaufmann , D. and Boese , R. 1990 . Angew. Chem. Int. Ed. Engl. , 29 : 545
  • Furuta , K. , Miwa , Y. , Iwanaga , K. and Yamamoto , H. 1988 . J. Am. Chem. Soc. , 110 : 6254
  • Furuta , K. , Shimizu , S. , Miwa , Y. and Yamamoto , H. 1989 . J. Org. Chem. , 54 : 1481
  • Takasu , M. and Yamamoto , H. 1990 . Synlett , : 194
  • Sartor , D. , Saffrich , J. and Helmchen , G. 1990 . Synlett , : 197
  • Kobayashi , S. , Murakami , M. , Harada , T. and Mukaiyama , T. 1991 . Chemistry Lett. , : 1341
  • Corey , E. J. and Loh , T. P. 1991 . J. Am. Chem. Soc. , 113 : 8966
  • Hawkins , J. M. and Loren , S. 1991 . J. Am. Chem. Soc. , 113 : 7794
  • Bir , G. and Kaufmann , D. 1987 . Tetrahedron Lett. , 28 : 777
  • Bir , G. and Kaufmann , D. 1990 . J. Organomet. Chem. , 390 : 1
  • Kelly , T. R. , Whiting , A. and Chandrakumar , N. S. 1986 . J. Am. Chem. Soc. , 108 : 3510
  • Maruoka , K. , Sakurai , M. , Fujiwara , J. and Yamamoto , H. 1986 . Tetrahedron Lett. , 27 : 4895
  • Ikota , N. , Tomioka , K. and Koga , K. 1987 . Tetrahedron Lett. , 28 : 5687
  • Northcott , C. J. and Valenta , Z. 1987 . Can. J. Chem. , 65 : 1917
  • Rebiere , F. , Riant , O. and Kagan , H. B. 1990 . Tetrahedron: Asymmetry , 1 : 199
  • Chapuis , C. and Jurczak , J. 1987 . Helv. Chim. Acta. , 70 : 436
  • Bao , J. , Wulff , W. D. and Rhenigold , A. L. 1993 . J. Am. Chem. Soc. , 115 : 1814
  • Corey , E. J. , Imwinkelried , R. , Pikul , S. and Xiang , Y. B. 1989 . J. Am. Chem. Soc. , 111 : 5493
  • Devine , P. N. and Oh , T. 1992 . J. Org. Chem. , 57 : 396
  • Narasaka , K. , Inoue , M. and Yamada , T. 1986 . Chemistry Lett. , : 1967 b) K. Narasaka, M. Inoue, T. Yamada, J. Sugimori and N. Iwasawa, ibid., 2409(1987). c) K. Narasaka, M. Inoue and N. Okada, ibid., 1109(1986). d) K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima and J. Sugimori, J. Am. Chem. Soc., 111, 5340(1989). e) K. Narasaka, H. Tanaka and F. Kanai, Bull. Chem. Soc. Jpn., 64, 387(1991).
  • Reetz , M. T. , Kyung , S. H. , Bolm , C. and Zierke , T. 1986 . Chem. Ind. (London) , : 824
  • Mikami , K. , Terada , M. , Motoyama , Y. and Nakai , T. 1991 . Tetrahedron Asymmetry , 2 : 643
  • Seebach , D. , Beck , A. K. , Imwinkelried , R. , Roggo , S. and Wonnacott , A. 1987 . Helv. Chim. Acta , 70 : 954
  • Maruoka , K. , Murase , N. and Yamamoto , H. 1993 . J. Org. Chem. , 58 : 2938
  • Iwasawa , N. , Hayashi , Y. , Sakurai , H. and Narasaka , K. 1989 . Chemistry Lett. , : 1581
  • Corey , E. J. , Imai , N. and Zhang , H. Y. 1991 . J. Am. Chem. Soc. , 113 : 728
  • Corey , E. J. and Ishihara , Kazuaki . 1992 . Tetrahedron Lett. , 33 : 6807
  • Khiar , N. , Fernandez , I. and Alcudia , F. 1993 . Tetrahedron Lett. , 34 : 123
  • Evans , D. A. , Woerpel , K. A.K. A. , Hinman , M. M. and Faul , M. M. 1991 . J. Am. Chem. Soc. , 113 : 726 b) R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005(1990). c) D. Muller, B. W. Umbricht, and A. Pfaltz, Helv. Chim. Acta, 74, 232(1991).
  • Evans , D. A. , Faul , M. M. , Bilodeau , M. T. , Anderson , B. A. and Barnes , D. M. 1993 . J. Am. Chem. Soc. , 115 : 5328
  • Evans , D. A. , Miller , S. J. and Lectka , T. 1993 . J. Am. Chem. Soc. , 115 : 6460
  • Kobayashi , S. , Hachiya , I. , Ishitani , H. and Araki , M. 1993 . Tetrahedron Lett. , 34 : 4535
  • Danishefsky , S. , Kerwin , J. F. Jr. and Kobayashi , S. 1982 . J. Am. Chem. Soc. , 104 : 358 b) S. Danishefsky, N. Kato, D. Askin and J. F. Kerwin Jr., ibid., 104, 360(1982). c) E. R. Larson and S. Danishefsky, Tetrahedron Lett., 23, 1975(1982). d) M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 105, 3716(1983).
  • Matsumoto , K. and Acheson , R. M. 1990 . “ Chapter 9 and 10 ” . In “Organic Synthesis at High Pressures” , 213 New York : John Wiley & Sons . b) N. S. Isaacs, Tetrahedron 47, 8463(1991)
  • Maruoka , K. , Itoh , T. , Shirasaka , T. and Yamamoto , H. 1988 . J. Am. Chem. Soc. , 110 : 310
  • Quimpere , M. and Jankowski , K. 1987 . Chem. Commun. , : 676
  • Gao , Q. , Maruyama , T. , Mouri , M. and Yamamoto , H. 1992 . J. Org. Chem. , 57 : 1951
  • Faller , J. W. and Smart , C. J. 1989 . Tetrahedron Lett. , 30 : 1189
  • Bednarski , M. and Danishefsky , S. 1983 . J. Am. Chem. Soc. , 105 : 6968
  • Bednarski , M. , Maring , C. and Danishefsky , S. 1983 . Tetrahedron Lett. , 24 : 3451
  • Bednarski , M. and Danishefsky , S. 1986 . J. Am. Chem. Soc. , 108 : 7060
  • Togni , A. 1990 . Organometallics , 9 : 3106
  • Togni , A. and Pastor , S. D. 1991 . Chirality , 3 : 331
  • Terada , M. , Mikami , K. and Nakai , T. 1991 . Tetrahedron Lett. , 32 : 935
  • Maruoka , K. and Yamamoto , H. 1988 . Tetrahedron , 44 : 5001 b). K. Maruoka, S. Nagahara and H. Yamamoto, J. Am. Chem. Soc., 112, 6115(1990). c) K. Maruoka, S. Nagahara and H. Yamamoto, Tetrahedron Lett., 31, 5475(1990). d) K. Maruoka, S. Saito and H. Yamamoto, J. Am. Chem. Soc., 114, 1089(1992).
  • Maruoka , K. and Yamamoto , H. 1989 . Tetrahedron , 111 : 789
  • Hattori , K. and Yamamoto , H. 1992 . J. Org. Chem. , 57 : 3264 b) K. Hattori and H. Yamamoto, Tetrahedron, 49, 1749(1993)
  • Roush , W. R. and Gillis , H. R. 1980 . J. Org. Chem. , 45 : 4267 b) W. R. Roush, H. Gillis and A. I. Ko, J. Am. Chem. Soc., 104, 2269(1982).
  • Iwasawa , N. , Sugimori , J. , Kawase , Y. and Narasaka , K. 1989 . Chemistry Lett. , : 1947
  • Narasaka , K. , Saitou , M. and Iwasawa , N. 1991 . Tetrahedron: Asymmetry , 2 : 1305
  • Furuta , K. , Kanematsu , A. , Yamamoto , H. and Takaoka , S. 1989 . Tetrahedron Lett. , 30 : 7231
  • Tietze , L. and Saling , P. 1992 . Synlett. , : 281
  • Nogradi , M. 1986 . “ Chapter 7.1.1 ” . In “Stereoselective Synthesis” , 266 New York : VCH .
  • Trost , B. M. , Fleming , I. and Paquette , L. A. 1991 . “ Chapter 1.10 ” . In “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry” , Vol 1 , 283 New York : Pergamon Press . For a more thorough discussion, see
  • Reetz , M. T. , Hullmann , M. , Massa , W. , Berger , S. , Rademacher , P. and Heymanns , P. 1986 . J. Am. Chem. Soc. , 108 : 2405
  • Corey , E. J. , Loh , T. P. , Sarshar , S. and Azimioara , M. 1992 . Tetrahedron Lett. , 33 : 6945
  • Shambayati , S. , Crowe , W. E. and Schreiber , S. L. 1990 . Angew. Chem. Int. Ed. Engl. , 29 : 256 For a review of X-ray crystallography studies, see
  • Houk , K. N. 1987 . J. Am. Chem. Soc. , 109 : 14 b) B. Gung and M. A. Wolf, J. Org. Chem., 57, 1370(1992).
  • Torri , J. and Azzaro , M. 1978 . Bull. Soc. Chim. Fr. , : 283
  • Fratiello , A. , Kubo , R. and Chow , S. 1976 . J. Chem. Soc. Perkin II , : 1205 For other solution studies of ketone-Lewis acid complexes see: b) J. S. Hartman and P. Stibs, Tetrahedron Lett., 3497(1975). c) A. Fratiello, G. Vidulich and Y. Chow, J. Org. Chem., 38, 2309(1973). d) U. Henriksson and S. Forsen, Chem. Commun., 1229(1970). f) R. F. Childs, L. Mulholland and A. Nixon, Can. J. Chem., 60, 801(1982)
  • Castellino , S. 1990 . J. Org. Chem. , 55 : 5197
  • Poll , T. , Metter , J. O. and Helrachen , G. 1985 . Angew. Chem. Int. Ed. Engl. , 24 : 112
  • Sartor , D. , Saffrich , J. and Helmchen , G. 1991 . Tetrahedron: Asymmetry , 2 : 639
  • Birney , D. M. and Houk , K. N. 1990 . J. Am. Chem. Soc. , 112 : 4127
  • Seerden , J. P.G. and Scheeren , H. W. 1993 . Tetrahedron Lett. , 34 : 2669
  • Takemura , H. , Komeshima , N. , Takahashi , I. , Hashimoto , S. , Ikota , N. , Tomioka , K. and Koga , K. 1987 . Tetrahedron Lett. , 28 : 5687
  • Northcott , C. J. and Valenta , Z. 1987 . Can. J. Chem. , 65 : 1917
  • Corey , E. J. , Sarshar , S. and Bordner , J. 1992 . J. Am. Chem. Soc. , 114 : 7938
  • Corey , E. J. and Matsumura , Y. 1991 . Tetrahedron Lett. , 32 : 6289
  • Narasaka , K. , Tanaka , H. and Kanai , F. 1991 . Bull. Chem. Soc. Jpn. , 64 : 387
  • Evans , D. A. , Woerpel , K. A. and Scott , M. J. 1992 . Angew. Chem. Int. Ed. Engl. , 31 : 430
  • Maruoka , K. , Nonoshita , K. and Yamamoto , H. 1988 . Syn. Commun. , 18 : 1453
  • Devine , P. N. 1992 . Ph. D. Dissertation Binghamton : SUNY .

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