Journal
NATURE CHEMISTRY
Volume 10, Issue 9, Pages 953-960Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41557-018-0080-1
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Funding
- NIH-NIGMS [R01 GM090007, R01 GM109078, F32 GM122245]
- National Science Foundation (NSF) [CHE-1361104, DGE-1144087]
- University of California, Los Angeles
- UCLA Cota Robles Fellowship Program
- Chemistry-Biology Interface training program [5T32GM008496-20]
- NSF [CHE-1048804, OCI-1053575]
- NIH NCRR [S10RR025631]
- UCLA Institute of Digital Research and Education (IDRE)
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361104] Funding Source: National Science Foundation
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For over a century, the structures and reactivities of strained organic compounds have captivated the chemical community. Whereas triple-bond-containing strained intermediates have been well studied, cyclic allenes have received far less attention. Additionally, studies of cyclic allenes that bear heteroatoms in the ring are scarce. We report an experimental and computational study of azacyclic allenes, which features syntheses of stable allene precursors, the mild generation and Diels-Alder trapping of the desired cyclic allenes, and explanations of the observed regio- and diastereoselectivities. Furthermore, we show that stereochemical information can be transferred from an enantioenriched silyl triflate starting material to a Diels-Alder cycloadduct by way of a stereochemically defined azacyclic allene intermediate. These studies demonstrate that heteroatom-containing cyclic allenes, despite previously being overlooked as valuable synthetic intermediates, may be harnessed for the construction of complex molecular scaffolds bearing multiple stereogenic centres.
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