1374855-53-4Relevant academic research and scientific papers
Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene
Zbieg, Jason R.,Yamaguchi, Eiji,McInturff, Emma L.,Krische, Michael J.
, p. 324 - 327 (2012)
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.
Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes
Yuan, Jinping,Jain, Pankaj,Antilla, Jon C.
, p. 12988 - 13003 (2020/11/23)
In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcohols (up to >99% enantiom
Iridium-catalyzed hydrohydroxyalkylation of butadiene: Carbonyl crotylation
Zbieg, Jason R.,Fukuzumi, Takeo,Krische, Michael J.
supporting information; experimental part, p. 2416 - 2420 (2010/12/25)
Exposure of alcohols 1a-1i to butadiene in the presence of a cyclometallated iridium catalyst derived from allyl acetate, 4-methoxy-3-nitrobenzoic acid and 2,2′-bis(diphenylphosphino)biphenyl (BIPHEP) results in hydrogen transfer to generate aldehyde-allyliridium pairs, which engage in C-C coupling to form products of carbonyl crotylation. Under related conditions using 1,4-butanediol as hydrogen donor, butadiene reductively couples to aldehydes 2e-2g and 2i to furnish carbonyl crotylation products 3e-3g and 3i. Thus, butadiene-mediated carbonyl crotylation occurs with equal facility from the alcohol or aldehyde oxidation level with complete levels of branched regioselectivity.
