Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 11
562
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Highly Enantioselective Diels–Alder Reaction Catalyzed by Chiral Imidazolidinone

, &
Pages 2032-2041 | Received 28 Aug 2008, Published online: 27 Apr 2009

REFERENCES

  • For reviews on enantioselective Diels–Alder reactions, see (a) Oppolzer , W. Asymmetric Diels–Alder and ene reactions in organic synthesis: New synthetic methods . Angew. Chem., Int. Ed. Engl. 1984 , 23 , 876 – 889 ; (b) Kagan , H. ; Riant , O. Catalytic asymmetric Diels–Alder reactions . Chem. Rev. 1992 , 92 , 1007 – 1019 ; (c) Corey , E. J. Catalytic enantioselective Diels–Alder reactions: Methods, mechanistic fundamentals, pathways, and applications . Angew. Chem., Int. Ed. Engl. 2002 , 41 , 1650 – 1667 .
  • (a) Wada , E. ; Pei , W. ; Kanemasa , S. Exclusively endo-selective Lewis acid–catalyzed hetero Diels–Alder reactions . Chem. Lett. 1994 , 2345 – 2350 ; (b) Pei , W. Chem. J. Chin. Univ. 1998 , 19 , 399 – 401 .
  • (a) Dalko , P. I. ; Moisan , L. In the golden age of organocatalysis . Angew. Chem., Int. Ed. Engl. 2004 , 43 , 5138 – 5175 ; (b) List , B. Organocatalysis: A complementary catalysis strategy advances organic synthesis . Adv. Synth. Catal. 2004 , 346 , 1021 ; (c) Houk , K. N. ; List , B. Asymmetric organocatalysis . Acc. Chem. Res. 2004 , 37 , 487 ; (d) Notz , W. ; Tanaka , F. ; Barbas , C. F. III . Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels–Alder reactions . Acc. Chem. Res. 2004 , 37 , 580 – 591 ; (e) Dalko , P. I. ; Moisan , L. Enantioselective organocatalysis . Angew. Chem., Int. Ed. Engl. 2001 , 40 , 3726 – 3748 ; (f) France , S. ; Guerin , D. J. ; Miller , S. J. ; Lectka , T. Nucleophilic chiral amines as catalysts in asymmetric synthesis . Chem. Rev. 2003 , 103 , 2985 – 3012 .
  • Ahrendt , K. A. ; Borths , C. J. ; MacMillan , D. W. C. New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels–Alder reaction . J. Am. Chem. Soc. 2000 , 122 , 4243 – 4244 .
  • (a) Corey , E. J. Catalytic enantioselective Diels–Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew. Chem., Int. Ed. Engl. 2002, 41, 1650; (b) Corey , E. J. ; Loh , T.-P. First application of attractive intramolecular interactions to the design of chiral catalysts for highly enantioselective Diels–Alder reactions. J. Am. Chem. Soc. 1991, 113, 8966–8967.
  • Mosse , S. ; Alexakis , A. Organocatalyzed asymmetric reactions via microwave activation . Org. Lett. 2006 , 8 , 3577 – 3580 .
  • Ishihara , K. ; Kurihara , H. ; Matsumoto , M. ; Yamamoto , H. Design of Br⊘nsted acid–assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels–Alder reactions . J. Am. Chem. Soc. 1998 , 120 , 6920 – 6930 .
  • Huang , Q. ; Xie , R. G. ; Tian , B. Z. ; Qing , S. Y. Synthetic Handbook of Organic Reagents, , 2nd ed.; Chemical Industry Press : Beijing , 2005 .

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.