Shapeshifting Gabriel Amine Synthesis with Iodo-BCPs
The Gabriel amine synthesis is a textbook method for the preparation of primary amines from alkyl halides. In this work, we demonstrate a Gabriel amine synthesis with iodo-bicyclopentanes to make aminomethyl bicyclobutanes. DFT studies support the concerted rearrangement of a bicyclo[1.1.1]pentyl to a bicyclo[1.1.0]butyl carbocation, initiated by a carbon-halide dissociation. A carboxamide substituent stabilizes the carbocation intermediate with anchimeric assistance.
Authors
- Michael D. Mandler (ORCID: https://orcid.org/0000-0003-4681-7473)
- Anuradha Gupta (ORCID: https://orcid.org/0000-0002-4211-1441)
- Mysore S. Pavan (ORCID: https://orcid.org/0000-0001-9751-7345)
- Nanjundaswamy K.C.
- Elizabeth A. Jurica (ORCID: https://orcid.org/0000-0003-3689-5451)
- Sourav Roy (ORCID: https://orcid.org/0000-0003-1885-3995)
- Ulaganathan Sankar
- Muthalagu Vetrichelvan (ORCID: https://orcid.org/0000-0001-7201-4143)
- James Mignone
- Kumar B. Pabbisetty (ORCID: https://orcid.org/0000-0001-9669-4059)
- Mohammad Javeed
- Sarah C. Traeger
- Antonio Ramı́rez (ORCID: https://orcid.org/0000-0003-2636-6855)
- Arvind Mathur (ORCID: https://orcid.org/0000-0002-7702-4006)
- Manivel Pitchai (ORCID: https://orcid.org/0000-0003-0749-0930)
Institutions
- Bristol-Myers Squibb (Germany) (DE)
- Bristol-Myers Squibb (United States) (US)
- Université Bourgogne Franche-Comté (FR)
- Bristol-Myers Squibb (India) (IN)
- Biocon (India) (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-21
- DOI
- https://doi.org/10.1021/acs.joc.5c00043
- Citations
- 2
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.87