Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 24
97
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Enantioselective Aldol‐Type Reaction Using Diketene

, , &
Pages 4487-4492 | Received 24 May 2004, Published online: 10 Jan 2011

References and Notes

  • Endo , A. , Kuroda , M. and Tsujita , Y. J. 1976 . Antibiot. , 29 : 1346
  • Brown , A. G. , Smale , T. C. , King , T. J. , Hasenkamp , R. and Thompson , R. H. 1976 . J. Chem. Soc., Perkin Trans. , : 1165
  • Hayashi , M. , Yoshimoto , K. , Hirata , N. , Tanaka , K. , Oguni , N. , Harada , K. , Matsushita , A. , Kawachi , Y. and Sasaki , H. 2002 . Isr. J. Chem. , 41 : 241
  • Singer , R. A. and Carreira , E. M. 1995 . J. Am. Chem. Soc. , 117 : 12360
  • De Rosa , M. , Soriente , A. and Scettri , A. 2000 . Tetrahedron: Asymmetry , 11 : 3187
  • Denmark , S. E. and Beutner , G. L. 2003 . J. Am. Chem. Soc. , 125 : 7800
  • Soriente , A. , De Rosa , M. , Stanzione , M. , Villano , R. and Scettri , A. 2001 . Tetrahedron: Asymmetry , 12 : 959
  • Izawa , T. and Mukaiyama , T. 1975 . Chem. Lett. , : 161
  • Oguni , N. , Tanaka , K. and Ishida , H. 1998 . Synlett , : 601
  • Hayashi , M. , Tanaka , K. and Oguni , N. 1995 . Tetrahedron: Asymmetry , 6 : 1833
  • Yanagisawa , A. , Matsumoto , Y. , Asakawa , K. and Yamamoto , H. 1999 . J. Am. Chem. Soc. , 121 : 892 Other catalytic aldol‐type reactions of diketene using BINAP have been reported:
  • Pu , L. 1998 . Chem. Rev. , 98 : 2405 For reviews on binaphthol and binaphthol‐titanium complexes, see:
  • The use of (S)‐BINOL and M(O‐i‐Pr)3 (M = Al, Y, La, Pr, Sm, Gd, Er, Yb), BH3, and Et2Zn resulted in low yields. In the case of catalyst derived from AlMe3, the reaction proceeded smoothly but enantiomeric excess was very low
  • Results of other titanium alkoxides; Ti(O‐n‐Bu)4 (29% ee), Ti(OEt)4 (22% ee), Ti(OMe)4 (5% ee)
  • Effect of reaction temperature: −20°C (37%, 23% ee, 96 h), −40°C (23%, 9% ee, 96 h), reflux (trace, 24 h). Result of other solvents: THF (30%, 23% ee, 24 h), ether (trace, 24 h), MeCN (trace, 24 h)
  • Results of reactions using other aldehydes under identical condition; 4‐methoxycinnnamaldehyde (31%, 83% ee), 2‐methoxycinnamaldehyde (34%, 73% ee), cyclohexanecarboxaldehyde (18%, 31% ee)
  • Benson , S. C. , Cai , P. , Colon , M. , Haiza , M. A. , Tokles , M. and Snyder , J. K. 1988 . J. Org. Chem. , 53 : 5335

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.