57951-63-0Relevant academic research and scientific papers
Cobalt-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt Homoenolates
Huang, Wei,Meng, Fanke
supporting information, p. 2694 - 2698 (2020/12/03)
Catalylic diastereo- and enantioselective hydroalkylation of 3,3-disubstituted cyclopropenes with Co-homoenolate generated in situ from ring-opening of easily accessible cyclopropanols promoted by a chiral phosphine–cobalt complex is presented. Such a process represents the unprecedented and direct introduction of a wide range of functionalized alkyl groups without the need of pre-formation of stoichiometric amounts of organometallic reagents onto the cyclopropane motif, affording multi-substituted cyclopropanes in up to 99 % yield with >95:5 dr and 98:2 er. Functionalization of the products delivered enantioenriched cyclopropanes that are otherwise difficult to access.
General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors
Jang, Yujin,Lindsay, Vincent N. G.,Poteat, Christopher M.,Rivera, Roger Machín
supporting information, (2020/09/02)
The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis of 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones. The transformation is shown to be amenable to sp-, sp2-, or sp3-hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.
Gold(I)-Catalyzed Ring Expansion of Alkynylcyclopropyl Allyl Ethers to Construct Tetrasubstituted Methylenecyclobutanones: A Mechanistic Investigation about the Character of Catalytic Amount of Water
Zang, Wenqing,Wang, Lei,Wei, Yin,Shi, Min,Guo, Yinlong
supporting information, p. 2321 - 2328 (2019/04/13)
A gold(I)-catalyzed ring expansion of alkynylcyclopropyl allyl ethers to produce tetrasubstituted methylenecyclobutanones in moderate to good yields has been disclosed in this paper. This reaction proceeded through an intramolecular [3,3]-sigmatropic rearrangement followed by [1,2]-allyl shift pathway in the presence of catalytic amount of water upon gold(I) catalysis. The intriguing reaction mechanism has been proposed on the basis of deuterium and 18O-labeling experiments, Mass spectroscopic analysis, 1H and 13C nuclear magnetic resonance (NMR) spectroscopic tracking and density functional theory (DFT) calculations. The further transformation of these methylenecyclobutanones into polycyclic skeleton has been realized by a practical three-step synthetic procedure. Several other transformations have been also indicated. (Figure presented.).
Visible-light-driven selective alkenyl C-P bond cleavage of allenylphosphine oxides
Wei, Kai,Luo, Kai,Liu, Fang,Wu, Lei,Wu, Li-Zhu
supporting information, p. 1994 - 1998 (2019/03/29)
An efficient method for highly selective alkenyl C-P bond cleavage, enabled by organic dyes and visible-light irradiation, was developed. This novel protocol involves a highly regioselective radical pathway initiated by singlet oxygen, affording diverse a
Rhodium(III)-Catalyzed Controllable C?H Bond Functionalization of Benzamides and Vinylidenecyclopropanes: A Directing Group Determined Reaction Pathway
Ji, Cheng,Xu, Qin,Shi, Min
supporting information, p. 974 - 983 (2017/03/27)
A controllable rhodium(III)-catalyzed C?H bond activation of benzamides and vinylidenecyclopropanes (VDCPs) by changing the directing group from C(O)NH–OPiv to C(O)NH–OBoc has been disclosed, affording two different major products in good yields under mild condition, respectively. The substrate scope has been investigated and a plausible reaction mechanism has been also proposed on the basis of previous literature. (Figure presented.).
A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
supporting information, p. 7493 - 7496 (2015/05/04)
Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
An efficient method for the synthesis of alkylidenecyclobutanones by gold-catalyzed oxidative ring enlargement of vinylidenecyclopropanes
Yuan, Wei,Dong, Xiang,Wei, Yin,Shi, Min
supporting information, p. 10501 - 10505 (2012/11/13)
Rings of gold: Vinylidenecyclopropanes can undergo efficient oxidative ring enlargements under mild conditions to give the corresponding alkylidenecyclobutanone derivatives in good yields (see scheme). A plausible mechanism for this transformation has bee
Regioselectivity switch: Gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones
Hashmi, A. Stephen K.,Wang, Tao,Shi, Shuai,Rudolph, Matthias
, p. 7761 - 7767 (2012/11/07)
The gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions. Pyridine-N-oxides were used as external oxidants with, different from related substrates, no alkylidenecycloalkanones or oxetan-3-ones formed as side-products.
Unprecedented consecutive, competitive nucleophilic addition to construct densely functionalized propargylic alcohols
Liu, Jie,An, Yan,Wang, Ya-Hui,Jiang, Hai-Ying,Zhang, Yu-Xin,Chen, Zili
supporting information; experimental part, p. 9131 - 9134 (2009/09/06)
An efficient one-pot process to construct a series of polyfunctionalized propargylic alcohol derivatives from the simple materials without functional protection was investigated. A solution of nBuLi in hexane was added into dry THF by syringe the resulting solution was then maintained at RT for 3 hours. the freshly prepared lithium enolate of acetaldehyde was used directly in the reaction. The nBuLi was added over a period of 30 minutes by syringe to a solution of terminal alkyne in THF at -30°C. The scope and limitations of the reaction was explored by examining other terminal alkynes. A number of different carbonyl-containing substrates were also examined. It was observed that propargylic alcohol derivatives are important synthetic intermediates in organic synthesis.
A convenient new method to construct 1-alkynyl cyclopropanol and its synthetic application to prepare trisubstituted dienones
An, Yan,Liu, Jie,Jiang, Hai-Ying,Wang, Yahui,Chen, Zili
, p. 3124 - 3128 (2008/09/20)
A new synthetic route was developed via the nucleophilic addition of lithium alkynylide to 1-arylsulfonyl cyclopropanol 1 to afford 1-alkynyl cyclopropanol, which then reacted with aryl iodide to construct trisubstituted cross-conjugated dienones through
