Journal
ORGANIC LETTERS
Volume 12, Issue 9, Pages 2088-2091Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100576m
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Funding
- NSF [CHE-0844602]
- DOE [DE-FC26-04NT42136]
- [ACS-PRF-47843-G1]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0844602] Funding Source: National Science Foundation
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The E-alpha-haloenones were prepared through a triazole-Au complex (TriA-Au) catalyzed propargyl acetate rearrangement and sequential allene halogenation. The reactions proceeded with only 1% catalyst loading, giving the challenging kinetic products in excellent yields and good to excellent stereoselectivity. These results not only provided the first example for the synthesis of challenging kinetic E-haloenones, but also revealed triazole Au complexes as effective catalysts in promoting chemoselective activation of alkynes over allenes.
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