Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 26, Pages 9178-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja904055z
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Funding
- NIGMS NIH HHS [R01 GM073932, R01 GM073932-04] Funding Source: Medline
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The asymmetric goid(I)-catatyzed ring expansion of 1-allenylcyclopropanots is described. The method provides synthetically valuable cyclobutanones with a vinyl-substituted quaternary stereogenic center in high enantiosetectivities and yields. The method shows a broad substrate scope, tolerating protected alcohols and amines, alkenes, unsaturated esters, and acetals. The reaction is easily adjustable to large-scale synthesis, leading to product formation without significant loss of selectivity or yield with only 0.5 mol% catalyst loading.
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