Hokkaido University · Chemistry
Professor Yoshihiro Sato's research lab specializes in transition-metal-catalyzed asymmetric synthesis, with a strong focus on the development of novel catalytic systems for stereoselective carbon-carbon bond formation. His group has made significant contributions to the fields of palladium- and nickel-catalyzed cyclizations, including [2+2+2] cocyclizations and three-component couplings, enabling efficient access to complex cyclic frameworks such as decalins, isoindolines, and arylnaphthalenes. The lab emphasizes the design of chiral ligands—particularly N-heterocyclic carbene (NHC) ligands—enabling high enantioselectivity and diastereoselectivity in these transformations. Their work has found key applications in the total synthesis of natural products, such as taiwanins C and E, highlighting the synthetic utility and precision of their methodologies.
Figures are computed from collected data and may differ slightly.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCatalytic asymmetric carbon-carbon bond formation: asymmetric synthesis of cis-decalin derivatives by palladium-catalyzed cyclization of prochiral alkenyl iodidesYoshihiro Sato, Mikiko Sodeoka, and Masakatsu ShibasakiCite this: J. Org. Chem. 1989, 54, 20, 4738–4739Publication Date (Print):September 1, 1989Publication History Published online1 May 2002Published inissue 1 September 1989https://pubs.acs.org/doi/10.1021/jo00281a007https://doi.org/10.1021/j
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAsymmetric Synthesis of Isoindoline and Isoquinoline Derivatives Using Nickel(0)-Catalyzed [2 + 2 + 2] CocyclizationYoshihiro Sato, Toyoki Nishimata, and Miwako MoriCite this: J. Org. Chem. 1994, 59, 21, 6133–6135Publication Date (Print):October 1, 1994Publication History Published online1 May 2002Published inissue 1 October 1994https://pubs.acs.org/doi/10.1021/jo00100a003https://doi.org/10.1021/jo00100a003research-articleACS PublicationsRequest reuse
Nickel(0)-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and silanes has been realized utilizing a chiral N-heterocyclic carbene as a ligand. On the basis of the screening of various NHC precursors, an imidazolium salt having 1-(2,4,6-trimethylphenyl)propyl groups on the nitrogen was designed and synthesized. In this reaction, various coupling products were produced in good yields with high regio-, diastereo- (anti selective in the case of the internal 1,3-diene), and en
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNovel Stereoselective Cyclization via .pi.-Allylnickel Complex Generated from 1,3-Diene and Hydride Nickel ComplexYoshihiro Sato, Masanori Takimoto, Koji Hayashi, Takao Katsuhara, Koji Takagi, and Miwako MoriCite this: J. Am. Chem. Soc. 1994, 116, 21, 9771–9772Publication Date (Print):October 1, 1994Publication History Published online1 May 2002Published inissue 1 October 1994https://pubs.acs.org/doi/10.1021/ja00100a061https://doi.org/10.1021/ja00100a0
3 in 1: A novel method for the synthesis of the arylnaphthalene skeleton by the Pd0-catalyzed [2+2+2] cocyclization of diynes and arynes involves three CC bond-forming reactions in a single step (see scheme; R=CON(OCH3)CH3, dba=dibenzylideneacetone). This cocyclization was the key step in the total synthesis of the arylnaphthalene lignans taiwanins C and E.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIon Imaging of the Photodissociation of OCS Near 217 and 230 nmYoshihiro Sato, Yutaka Matsumi, Masahiro Kawasaki, Koichi Tsukiyama, and Richard BersohnCite this: J. Phys. Chem. 1995, 99, 44, 16307–16314Publication Date (Print):November 1, 1995Publication History Published online1 May 2002Published inissue 1 November 1995https://pubs.acs.org/doi/10.1021/j100044a017https://doi.org/10.1021/j100044a017research-articleACS PublicationsRequest reuse permissio
A nickel-promoted intramolecular cyclization of 1,3-diene with the tethered carbonyl group was developed using the catalyst generated by reduction of Ni(acac)2 with DIBAL-H in the presence of PPh3. It was found that the addition of 1,3-CHD to the reaction mixture affected the regiochemistry of olefin on the side chain of the cyclized product. The reaction course of this cyclization can be accounted for by two possible mechanisms. In one mechanism, a nickel hydride complex plays a key role and th
Various allylic alcohols were carboxylated in the presence of a catalytic amount of PdCl2 and PPh3 using ZnEt2 as a stoichiometric transmetalation agent under a CO2 atmosphere (1 atm). This carboxylation proceeded in a highly regioselective manner to afford branched carboxylic acids predominantly. The β,γ-unsaturated carboxylic acid thus obtained was successfully converted into an optically active γ-butyrolactone, a known intermediate of (R)-baclofen.
It′s a gas: A novel one-pot process for the synthesis of α-amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl. Detailed facts of importance to specialist reade
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTA Novel Asymmetric Cyclization of ω-Formyl-1,3-dienes Catalyzed by a Zerovalent Nickel Complex in the Presence of SilanesYoshihiro Sato, Nozomi Saito, and Miwako MoriView Author Information Graduate School of Pharmaceutical Sciences Hokkaido University, Sapporo 060-0812, Japan Cite this: J. Am. Chem. Soc. 2000, 122, 10, 2371–2372Publication Date (Web):February 25, 2000Publication History Received19 November 1999Published online25 February 2000Pub
Three-in-one: The nickel-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and a silylborane in the presence of a chiral phosphoroamidite ligand has been realized. The reaction proceeds by σ-bond metathesis of an oxanickelacycle intermediate with the silylborane to afford the corresponding α-chiral allylsilane derivative in a highly diastereo- and enantioselective manner. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such docu
The use of N-heterocyclic carbene 2 as a ligand in a nickel(0)-catalyzed coupling reaction of 1,3-diene and aldehyde was investigated. It was found that the Ni(0)−carbene complex showed a unique property in the reaction of 1,3-diene 4 and aldehyde 5 to give the coupling product Z-6, having a (Z)-olefin in high yield in a highly stereoselective manner. Since the same reaction using the Ni(0)−PPh3 complex gave E-6a in a stereoselective manner, this result indicates that the Ni(0)−carbene complex h
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