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Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.

ABSTRACT: 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 × 10(6) 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.

SUBMITTER: Zbieg JR

PROVIDER: S-EPMC3439217 | biostudies-other | 2012 Apr

REPOSITORIES: biostudies-other

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Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.

Zbieg Jason R JR Yamaguchi Eiji E McInturff Emma L EL Krische Michael J MJ

Science (New York, N.Y.) 20120322 6079

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 × 10(6) 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 level ...[more]

PMID: 22442385

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