Journal
TETRAHEDRON
Volume 71, Issue 26-27, Pages 4413-4417Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.03.012
Keywords
Rhazinilam; Nickel; Aluminum; Carbocyanation; C-C bond activation
Categories
Funding
- Ministry of Education, Culture, Sports, Science, and Technology [22105003]
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [22105003] Funding Source: KAKEN
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Intramolecular arylcyanation across a tri-substituted double bond proceeds to give a primary alkyl cyanide product through functionalization of C-CN and allylic C-H bonds and double C-C bond formation in a 1,3-manner by cooperative nickel/AlMe2Cl catalysis. The transformation is applied to the synthesis of rhazinilam, a tubulin-binding alkaloid containing unique structural motifs such as axially chiral biaryl and strained nine-membered lactam as well as quaternary carbon. (C) 2015 Elsevier Ltd. All rights reserved.
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