화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Applied Chemistry for Engineering, Vol.25, No.5, 437-446, October, 2014
Export Citation
비고리 알릴아민 화합물의 입체선택적 이중알코올화 반응
Stereocontrolled Dihydroxylation Reactions of Acyclic Allylic Amines
전종호†, 신나라1, 김영규1, †
  • 한국원자력연구원 첨단방사선연구소 생명공학연구부
  • 1서울대학교 공과대학 화학생물공학부
Jongho Jeon†, Nara Shin1, and Young Gyu Kim1, †
  • Research Division for Biotechnology, Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 580-185 Republic of Korea
  • 1Department of Chemical and Biological Engineering, Seoul National University, Seoul 157-744 Republic of Korea
E-mail:,
초록
비고리 알릴아민 화합물의 이중알코올화 반응은 아미노 다이올 구조를 도입할 수 있는 효율적인 합성법으로 아미노다이올 구조를 포함하는 다양한 생리활성 천연물의 효율적인 합성에 적용될 수 있다. 본 리뷰에서는 기질 그 자체, 혹은 카이랄 리간드를 이용한 다양한 입체선택적 이중알코올화 반응들을 소개하고 이를 실제 천연물의 합성에 적용한 최근의 반응 결과들을 살펴보고자 한다.
The dihydroxylation reaction of allylic amines is a facile and useful synthetic method to obtain amino diol structures that are widely found in lots of biologically important natural products. This review will focus on the recent methods of both substrate-controlled and ligand-controlled dihydroxylation reactions of acyclic allylic amines. In addition, several applications of the diastereoselective dihydroxylation methods to asymmetric syntheses of natural products are presented.
Keywords:Dihydroxylation;Acyclic conformation;Asymmetric synthesis;Natural product;Osmium tetroxide
  1. Bergmeier SC, Tetrahedron, 56, 2561 (2000)
  2. Ager DJ, Prakash I, Schaad DR, Chem. Rev., 96(2), 835 (1996)
  3. Cha JK, Kim NS, Chem. Rev., 95(6), 1761 (1995)
  4. Cha JK, Christ WJ, Kishi Y, Tetrahedron Lett., 24, 3943 (1983)
  5. Christ WJ, Cha JK, Kishi Y, Tetrahedron Lett., 24, 3947 (1983)
  6. Cha JK, Christ WJ, Kishi Y, Tetrahedron, 40, 2247 (1984)
  7. Houk KN, Duh HY, Wu YD, Moses SR, J. Am. Chem. Soc., 108, 2754 (1986)
  8. Vedejs E, McClure CK, J. Am. Chem. Soc., 108, 1094 (1986)
  9. Donohoe TJ, Blades K, Helliwell M, Moore PR, Winter JJG, J. Org. Chem., 64, 2980 (1999)
  10. Donohoe TJ, Blades K, Moore PR, Waring MJ, Winter JJG, Helliwell M, Newcombe NJ, Stemp G, J. Org. Chem., 67, 7946 (2002)
  11. Olsen JA, Severinsen R, Rasmussen TB, Hentzer M, Givskov M, Nielsen J, Bioorg. Med. Chem. Lett., 12, 325 (2002)
  12. Oh JS, Park DY, Song BS, Bae JG, Yoon SW, Kim YG, Tetrahedron Lett., 43, 7209 (2002)
  13. Imashiro R, Sakurai O, Yamashita T, Horikawa H, Tetrahedron, 54, 10657 (1998)
  14. Shirota O, Nakanishi K, Berova N, Tetrahedron, 55, 13643 (1999)
  15. Matsuura F, Hamada Y, Shioiri T, Tetrahedron Lett., 35, 733 (1994)
  16. Shuter EC, Duong H, Hutton CA, McLeod MD, Org. Biomol. Chem., 5, 3183 (2007)
  17. Churches QI, White JM, Hutton CA, Org. Lett., 13, 2900 (2011)
  18. Llaveria J, Diaz Y, Matheu MI, Castillon S, Org. Lett., 11, 205 (2009)
  19. Hama N, Aoki T, Miwa S, Yamazaki M, Sato T, Chida N, Org. Lett., 13, 616 (2011)
  20. Csatayova K, Davies SG, Lee JA, Roberts PM, Russell AJ, Thomson JE, Wilson DL, Org. Lett., 13, 2606 (2011)
  21. Davies SG, Fletcher AM, Foster EM, Lee JA, Roberts PM, Thomson JE, J. Org. Chem., 78, 2500 (2013)
  22. Yoshimitsu Y, Inuki S, Oishi S, Fujii N, Ohno H, J. Org. Chem., 75, 3843 (2010)
  23. Yang G, Schmieg J, Tsuji M, Franck RW, Angew. Chem. Int. Ed., 43, 3818 (2004)
  24. Csatayova K, Davies SG, Ford JG, Lee JA, Roberts PM, Thomson JE, J. Org. Chem., 78, 12397 (2013)
  25. Jeon J, Shin M, Yoo JW, Oh JS, Bae JG, Jung SH, Kim YG, Tetrahedron Lett., 48, 1105 (2007)
  26. Reetz MT, Strack TJ, Mutulis F, Goddard R, Tetrahedron Lett., 37, 9293 (1996)
  27. Broady SD, Rexhausen JE, Thomas EJ, J. Chem. Soc., Perkin Trans., 1, 1083 (1999)
  28. Reddy JS, Rao BV, sort A, J. Org. Chem., 72, 2224 (2007)
  29. Kotkar SP, Chavan VB, Sudalai A, Org. Lett., 9, 1001 (2007)
  30. Martin R, Murruzzu C, Pericas MA, Riera A, J. Org. Chem., 70, 2325 (2005)
  31. Huang Y, Dalton DR, J. Org. Chem., 62, 372 (1997)
  32. Dondoni A, Merino P, Perrone D, Tetrahedron, 49, 2939 (1993)
  33. Shinada T, Ikebe E, Oe K, Namba K, Kawasaki M, Ohfune Y, Org. Lett., 9, 1765 (2007)
  34. Lee YJ, Park Y, Kim MH, Jew SS, Park HG, J. Org. Chem., 76, 740 (2011)
  35. Olivier KS, Van Nieuwenhze MS, Org. Lett., 12, 1680 (2010)
  36. Hulme AN, Montgomery CH, Tetrahedron Lett., 44, 7649 (2003)
  37. Coutrot P, Claudel S, Didierjean C, Grison C, Bioorg. Med. Chem. Lett., 16, 417 (2006)
  38. Thoen JC, Morales-Ramos AI, Lipton MA, Org. Lett., 4, 4455 (2002)
  39. Oh JS, Jeon J, Park DY, Kim YG, Chem. Commun., 41, 771 (2005)
  40. Jeon J, Hong SK, Oh JS, Kim YG, J. Org. Chem., 71, 3310 (2006)
  41. Jeon J, Lee JH, Kim JW, Kim YG, Tetrahedron: Asymmetry, 18, 2448 (2007)
  42. Jeon J, Shin N, Lee JH, Kim YG, Appl. Chem. Eng., 25(4), 392 (2014)
  43. Jeon J, Kim SH, Lee JH, Kim YG, Bull. Korean Chem. Soc., 30, 1003 (2009)