Journal
ORGANIC LETTERS
Volume 18, Issue 3, Pages 460-463Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03503
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Funding
- NSF [CHE-1362959]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1362959] Funding Source: National Science Foundation
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Photogenerated aza-o-xylylenes undergo intramolecular cycloaddition reactions to tethered oxazoles, with primary photoproducts featuring a reactive cyclic imine moiety suitable for multicomponent postphotochemical transformations. For example, the reaction of these imine photoproducts with bromoacetyl bromide leads to a key 1,4-dielectrophilic synthon, offering access to diverse polyheterocyclic molecular architectures. This reaction sequence is accompanied by rapid growth complexity in a very few simple synthetic steps, and is in keeping with the philosophy of diversity oriented synthesis (DOS).
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