Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 7
167
Views
40
CrossRef citations to date
0
Altmetric
Original Articles

Manganese-Promoted, Titanocene-Catalyzed Stereoselective Pinacol Coupling of Aldehydes

&
Pages 1097-1106 | Received 23 Sep 1998, Published online: 17 Sep 2007

References

  • Robertson , G. M. 1991 . “Pinacol Coupling Reactions” . In Comprehensive Organic Synthesis , Edited by: Trost , B. M. vol. 3 , London : Pergamon Press . chap. 2.6 of, Review:
  • Handa , Y. and Inanaga , J. 1987 . Tetrahedron Lett. , 46 : 5717 Ti-based:.
  • Barden , M. C. and Schwartz , J. 1996 . J Am. Chem. Soc. , 118 : 5484
  • Clerici , A. , Clerici , L. and Porta , O. 1996 . Tetrahedron Lett. , 37 : 3035
  • Szymoniac , J. , Besancon , J. and Moise , C. 1994 . Tetrahedron , 50 : 2841 Nb-based:.
  • Kammermeier , B. , Beck , G. , Jacobi , D. and Jendralla , H. 1994 . Angew. Chem. Int. Ed. Engl. , 33 : 685 V-based:.
  • Kempf , D. J. , Sowin , T. J. , Doherty , E. M. , Hannick , S. M. , Codavoci , L. , Henry , R. F. , Green , B. E. , Spanton , S. G. and Norbeck , D. W. 1992 . J. Org. Chem. , 57 : 5692
  • Konradi , A. W. , Kemp , S. J. and Pedersen , S. F. 1994 . J. Am. Chem. Soc. , 116 : 1316
  • Barden , M. C. and Schwartz , J. 1997 . J. Org. Chem. , 62 : 7520 Zr-based:.
  • Halterman , R. L. 1992 . Chem. Rev. , 92 : 965
  • Gansäuer , A. J. 1997 . Chem. Soc. Chem. Commun. , : 457
  • Gansauer , A. 1997 . Synlett , : 363
  • Gansauer , A. and Bauer , D. 1998 . J. Org. Chem. , 63 : 2070
  • Lipski , T. A. , Hilfriker , M. A. and Nelson , S. G. 1997 . J. Org. Chem. , 62 : 4566
  • Hirao , T. , Asahara , M. , Muguruma , Y. and Ogawa , A. 1998 . J. Org. Chem. , 63 : 2812
  • Stereochemistry was assigned by hydrolysis to dUmeso hydrobenzoin and comparison with authentic commercial samples
  • We have found that the diastereoselectivity in the pinacol coupling of benzaldehyde by Zn/TMSCl /Cp2TiCl2 (ref. 7a) depends markedly on the source of Zn because competing direct Zn-induced coupling (ref. 12) which occurs with little stereoselectivity
  • So , J-H. , Park , M-K. and Boudjouk , P. 1988 . J Org. Chem. , 53 : 5871
  • Cahiez , G. and Chavant , P. Y. 1989 . Tetrahedron Lett. , 30 : 7373 Mn has been receiving increasing attention as a selective reducing agent; see e.g. Hiyama, T., Obayashi, M., Makamura, A. Organometallics 1982, 1 1249; Furstner, A., Brunner, H. Tetrahedron Lett. 1996, 37 7009; Ueda, T., Ikeda, N., Moriwake, T. J. Org. Chem. 1996, 61 7990
  • 1981-2 . Registry of Toxic Effects of Chemical Substances vol. 2 , toxicity:, NIOSH
  • Li , C. J. , Meng , Y. , Yi , X. H. , Ma , J. and Chan , T. H. 1997 . J. Org. Chem. , 62 : 8632 Although no reaction between cyclohexanecarboxaldehyde and Mn/TMSCl/THF was detected after several hours at 20 °C, Mn has been reported to pinacolize aromatic aldehydes in aqueous media (with negligible stereoselectivity); see
  • Schäfer , A. , Karl , E. , Zsolnai , L. , Huttner , G. and Brintzinger , H. H. 1987 . J. Organomet. Chem. , 328 : 87
  • Coutts , R. S.P. , Martin , R. L. and Wailes , P. C. 1973 . J. Organomet. Chem. , 47 : 380
  • Sekutowski , D. , Jungst , R. and Stucky , G. D. 1978 . Inorg. Chem. , 17 : 1848
  • Souppe , J. , Danon , L. , Namy , J. L. and Kagan , H. B. 1983 . J Organomet. Chem. , 250 : 227 Hoffmann, R.W., Ditrich, K., Koster, G., Sturmer, R. Chem Ber. 1989, 722, 1783

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.