Journal article
Stereoselective Synthesis of ( E )- and ( Z )-Isocyanoalkenes
Organic letters, v 24(47), pp 8657-8661
02 Dec 2022
PMID: 36399331
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
(
)- and (
)-isocyanoalkenes were selectively synthesized via the sequential cross coupling of vinyl iodides with formamide, followed by dehydration. The optimal catalyst, generated in situ from Cu
I and
-dimethyl-1,2-cyclohexanediamine, rapidly coupled (
)- or (
)-vinyl iodides with formamide, which minimized the isomerization of the resultant vinyl formamide. The method efficiently provided a range of acyclic, carbocyclic, and heterocyclic isocyanoalkenes; the versatility is illustrated with the selective, stereodivergent syntheses of the diastereomeric isocyanoalkene antibiotics, B371 and
-B371.
Metrics
Details
- Title
- Stereoselective Synthesis of ( E )- and ( Z )-Isocyanoalkenes
- Creators
- Huan Tian - Drexel UniversityCaleb W Holyoke, Jr - Department of Chemistry, Drexel University, 3141 Chestnut Street, Philadelphia, Pennsylvania 19104, United StatesFraser F Fleming - Drexel University
- Publication Details
- Organic letters, v 24(47), pp 8657-8661
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000889560300001
- Scopus ID
- 2-s2.0-85142621109
- Other Identifier
- 991020898500904721
UN Sustainable Development Goals (SDGs)
This publication has contributed to the advancement of the following goals:
InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Web of Science research areas
- Chemistry, Organic