Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 25, Pages 8722-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9041302
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Funding
- NIGMS NIH HHS [GM58877] Funding Source: Medline
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The transition metal catalyzed allylic amination represents a powerful and versatile cross-coupling for the asymmetric construction of stereogenic C-N bonds that are present in secondary metabolites and medicinally important agents. We have developed a regio- and enantiospecific rhodium-catalyzed allylic amination reaction using the azaylide derived from 1-aminopyridinium iodide. This investigation demonstrates the importance of the ylide-stabilizing group for obtaining the desired nucleophilicity and the ability to utilize the aza-ylide as a commercially available ammonia equivalent, which serves to illustrate the synthetic potential of this nucleophile for the preparation of primary amines. Overall, this work provides an opportunity to investigate the utility of this new class of nucleophiles in related metal-catalyzed reactions.
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