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

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Science  20 Apr 2012:
Vol. 336, Issue 6079, pp. 324-327
DOI: 10.1126/science.1219274

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The direct, by-product–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 an enormous scale (about 12 × 106 metric tons annually). Here, with the use of 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 by-products.

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