Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 15, Pages 5752-5755Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja201035b
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Funding
- National Institute of General Medical Sciences
- National Institutes of Health [GM-36700]
- National Science Foundation [CHE-0955864]
- DuPont
- Boehringer Ingelheim
- Eli Lilly
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The mechanisms of the Fischer indole synthesis and competing cleavage pathways were explored with SCS-MP2/6-31G(d) and aqueous solvation calculations. Electron-donating substituents divert the reaction pathway to heterolytic N-N bond cleavage and preclude the acid-promoted [3,3]-sigmatropic rearrangement.
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