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Letter

Conformational Effects in Diastereoselective Aryne Diels−Alder Reactions: Synthesis of Benzo-Fused [2.2.1] Heterobicycles

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Robert Webster and Mark Lautens

Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6

Org. Lett., 2009, 11 (20), pp 4688–4691

DOI: 10.1021/ol9019869

Publication Date (Web): September 24, 2009

mlautens@chem.utoronto.ca

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

It was found that the diastereoselectivity of the Diels−Alder reaction between arynes and substituted furans is highly sensitive to substitution, which affects the reactive conformation. By varying the location of the groups on the diene partner, it is possible to obtain both excellent chemical yields and high stereoselectivity. This methodology offers rapid and convenient access to enantiomerically pure bicyclic scaffolds which are difficult to prepare by other means.

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Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies
David A. Candito, Jane Panteleev, and Mark Lautens
Journal of the American Chemical Society2011 Article ASAP
- Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies
  David A. Candito, Jane Panteleev, and Mark Lautens
  Journal of the American Chemical Society2011 Article ASAP
  Although the chemistry of arynes is well developed, some challenges still remain. The ene reaction of arynes has not gained widespread use in synthesis as a result of poor yields and selectivity. A general, high yielding and selective intramolecular aryne–...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Opioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin A
Anthony Lozama, Christopher W. Cunningham, Michael J. Caspers, Justin T. Douglas, Christina M. Dersch, Richard B. Rothman, and Thomas E. Prisinzano
Journal of Natural Products2011 74 (4), 718-726
- Opioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin A
  Anthony Lozama, Christopher W. Cunningham, Michael J. Caspers, Justin T. Douglas, Christina M. Dersch, Richard B. Rothman, and Thomas E. Prisinzano
  Journal of Natural Products2011 74 (4), 718-726
  As part of our continuing efforts toward more fully understanding the structure−activity relationships of the neoclerodane diterpene salvinorin A, we report the synthesis and biological characterization of unique cycloadducts through [4+2] Diels−Alder ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted Allenamides
Andrew G. Lohse, Richard P. Hsung, Mitchell D. Leider, and Sunil K. Ghosh
The Journal of Organic Chemistry2011 Article ASAP
- Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted Allenamides
  Andrew G. Lohse, Richard P. Hsung, Mitchell D. Leider, and Sunil K. Ghosh
  The Journal of Organic Chemistry2011 Article ASAP
  Efforts toward achieving a practical and diastereoselective intramolecular [4 + 3] cycloaddition of nitrogen-stabilized oxyallyl cations with tethered dienes are described. Epoxidation of N-sulfonyl substituted allenamides with dimethyldioxirane (DMDO) ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Construction of All-Carbon Quaternary Center by R₂AlCl−Mediated Ring-Opening Reaction of Oxacycles
Chao Che, Lianzhu Liu, Jianxian Gong, Yunfang Yang, Guoxin Wang, Junmin Quan and Zhen Yang
Organic Letters2010 12 (3), 488-491
- Construction of All-Carbon Quaternary Center by R₂AlCl−Mediated Ring-Opening Reaction of Oxacycles
  Chao Che, Lianzhu Liu, Jianxian Gong, Yunfang Yang, Guoxin Wang, Junmin Quan and Zhen Yang
  Organic Letters2010 12 (3), 488-491
  An unexpected R2AlCl-mediated ring-opening reaction of oxacycles for the formation of all-carbon quaternary centers was discovered, and a possible mechanism is proposed. The developed chemistry provides a concise approach to synthesize structural ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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History

Published In Issue October 15, 2009
Article ASAPSeptember 24, 2009
Received: August 26, 2009

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Letter

Conformational Effects in Diastereoselective Aryne Diels−Alder Reactions: Synthesis of Benzo-Fused [2.2.1] Heterobicycles

Abstract

Citing Articles

Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies

Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies

Opioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin A

Opioid Receptor Probes Derived from Cycloaddition of the Hallucinogen Natural Product Salvinorin A

Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted Allenamides

Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted Allenamides

Construction of All-Carbon Quaternary Center by R₂AlCl−Mediated Ring-Opening Reaction of Oxacycles