title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
authors.forename: Jason R
authors.initials: JR
authors.lastname: Zbieg
authors.forename: Eiji
authors.initials: E
authors.lastname: Yamaguchi
authors.forename: Emma L
authors.initials: EL
authors.lastname: McInturff
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D002070:Butadienes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D010710:Phosphates / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D002070:Butadienes; D010710:Phosphates; D002244:Carbon; D012428:Ruthenium; D006859:Hydrogen