100571-53-7Relevant academic research and scientific papers
Diboration of 3-substituted propargylic alcohols using a bimetallic catalyst system: access to (Z)-allyl, vinyldiboronates
Peck, Cheryl L.,Nekvinda, Jan,Santos, Webster L.
supporting information, p. 10313 - 10316 (2020/09/16)
The diboration of substituted propargylic alcohols has been achieved using a bimetallic Pd/Cu catalyst system. Thein situformation of a pentrafluoroboronic acid intermediate sufficiently activates the C-O bond towards dual catalysis affording (Z)-allyl, vinyldiboronates stereoselectively.
Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen
Pape, Felix,Brechmann, Lea T.,Teichert, Johannes F.
supporting information, p. 985 - 988 (2019/01/04)
Copper(I)–N-heterocyclic-carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation.
Gold(III)-Catalyzed Regioselective Oxidation/Cycloisomerization of Diynes: An Approach to Fused Furan Derivatives
Li, Jian,Xing, Hong-Wen,Yang, Fang,Chen, Zi-Sheng,Ji, Kegong
, p. 4622 - 4626 (2018/08/07)
The first gold(III)-catalyzed regioselective oxidation/cycloisomerization of diynes 1 with pyridine N-oxide as the oxidant was developed, providing a range of synthetically valuable and useful fused furan derivatives 3 in moderate to good yields. Control experiments and the confirmation structure of minor products 5 suggest that this chemistry was a concerted gold(III)-catalyzed oxidation/SN2′-type addition/cyclization process via a β-gold vinyloxypyridinium intermediate and a putative vinyl cation intermediate.
Z-Selective Copper(I)-Catalyzed Alkyne Semihydrogenation with Tethered Cu-Alkoxide Complexes
Pape, Felix,Thiel, Niklas O.,Teichert, Johannes F.
, p. 15934 - 15938 (2015/11/03)
A highly stereoselective alkyne semihydrogenation with copper(I) complexes is reported. Copper-N-heterocyclic carbene complex catalysts, bearing an intramolecular Cu-O bond, allow for the direct transfer of both hydrogen atoms from dihydrogen to the alkyn
Enantioselective total synthesis of aigialomycin D
Lu, Jiangping,Ma, Junying,Xie, Xingang,Chen, Bo,She, Xuegong,Pan, Xinfu
, p. 1066 - 1073 (2007/10/03)
An efficient, convergent approach for the total synthesis of aigialomycin D 1 is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hy
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
The Synthesis of Cembranolide Precursors via Addition of Allylstannanes to Conjugated Aldehydes
Marshall, James A.,DeHoff, Bradley S.
, p. 863 - 872 (2007/10/02)
The Lewis acid promoted addition of functionalized allylstannanes A9, C10, and C11 to a variety of conjugated aldehydes was examined as a possible route to acyclic precursors of macrocyclic diterpenoids.Additions to crotonaldehyde proceeded as expected, g
