3558-06-3Relevant articles and documents
Sterically Unprotected Nucleophilic Boron Cluster Reagents
Mu, Xin,Axtell, Jonathan C.,Bernier, Nicholas A.,Kirlikovali, Kent O.,Jung, Dahee,Umanzor, Alexander,Qian, Kevin,Chen, Xiangyang,Bay, Katherine L.,Kirollos, Monica,Rheingold, Arnold L.,Houk,Spokoyny, Alexander M.
supporting information, p. 2461 - 2469 (2019/09/10)
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Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C?H Insertion of Donor/Donor Carbenes
Souza, Lucas W.,Squitieri, Richard A.,Dimirjian, Christine A.,Hodur, Blanka M.,Nickerson, Leslie A.,Penrod, Corinne N.,Cordova, Jesus,Fettinger, James C.,Shaw, Jared T.
supporting information, p. 15213 - 15216 (2018/10/31)
We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C?H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C?H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.
Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure
Roque Pena, Joan E.,Alexanian, Erik J.
supporting information, p. 4413 - 4415 (2017/09/11)
A catalytic preparation of silyl enol ethers from unactivated secondary alkyl tosylates is reported. An inexpensive cobalt catalyst is used under mild conditions with low pressures of carbon monoxide. Nucleophilic, anionic cobalt carbonyls facilitate the catalytic activation of a range of alkyl tosylates. The silylcarbonylation offers a practical approach to synthetically valuable silyl enol ethers from simple starting materials.