Regioselective dicouplings: Application to differentially substituted pyrroles

Organic Letters

Volumn 8, Issue 8, 2006, Pages 1537-1539

  Handy, Scott T ^a,b   Sabatini, Jesse J ^a  

^a BINGHAMTON UNIVERSITY   (United States)

^b MIDDLE TENNESSEE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646456316     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0530981     Document Type: Article

References (12)

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3. Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085-2086.
4. Duan, X.-F.; Li, X.-H.; Li, F.-Y.; Huang, C.-H. Synthesis 2004, 2614-2617.
5. Fauvarque, J.-F.; Pfleuger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419-427.
6. Handy, S. T.; Bregman, H.; Lewis, J.; Zhang, Y. Tetrahedron Lett. 2003, 44, 427-430.
7. Anderson, H. J.; Lee, S.-F. Can. J. Chem. 1965, 43, 409-414.
8. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
9. Interestingly, allyl and benzyl protecting groups caused the reaction to only proceed part of the way to completion and, in the case of the allyl protecting group, completely shut down the second coupling, even under the added phosphine conditions. The origin of this change in behavior is the object of current study.
10. Lamellarins: Handy, S. T.; Zhang, Y. Org. Prep. Proced. Int. 2005, 37, 411-445.
11. Prodigiosins: Fuerstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
12. Lipitor: Li, J. J.; Johnson, D. S.; Sliskovic, D. R.; Roth, B. D. Contemporary Drug Synthesis; Wiley-Interscience: New York, 2004; pp 113-124.