Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene

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Science  22 Mar 2012:
DOI: 10.1126/science.1219274

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The direct, byproduct-free conversion of basic feedstocks to products of medicinal and agricultural relevance is a broad goal of chemical research. Butadiene is a product of petroleum cracking and is produced on enormous scale (about 12 × 109 metric tons annually). Here, using a ruthenium catalyst modified by a chiral phosphate counterion, we report the direct redox-triggered carbon-carbon coupling of alcohols and butadiene to form products of carbonyl crotylation with high levels of anti-diastereoselectivity and enantioselectivity in the absence of stoichiometric byproducts.

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