Jung-Woo Park, Zhiwei Chen, and Vy M. Dong
J. Am. Chem. Soc., 2016, 138 (10), pp 3310–3313
Publication Date (Web): March 8, 2016 (Communication)
DOI: 10.1021/jacs.6b01445
We report a Rh-catalyzed enantioselective cycloisomerization of α,ω-heptadienes to afford cyclohexenes bearing quaternary carbon centers. Rhodium(I) and a new SDP ligand promote chemoselective formation of a cyclohex-3-enecarbaldehyde motif that is ...
Peter G. Gildner, Andrew DeAngelis, and Thomas J. Colacot
Org. Lett., 2016, 18 (6), pp 1442–1445
Publication Date (Web): March 2, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00377
A general method has been developed for the previously challenging arylation of cyclopropylamine and N-arylcyclopropylamines. Highly active, air-stable, and commercially available R-allylpalladium precatalysts provide access to a wide range of (hetero)...
Luisa Lempenauer, Elisabet Duñach, and Gilles Lemière
Org. Lett., 2016, 18 (6), pp 1326–1329
Publication Date (Web): March 1, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00270
A catalytic rearrangement of diallyl alcohols comprising a cyclic enol ether has been developed using very mild conditions. Bismuth(III) triflate was found to be a very active catalyst for the ring rearrangement of a range of tertiary allylic alcohols to ...
Natasha F. O’Rourke and Glenn C. Micalizio
Org. Lett., 2016, 18 (6), pp 1250–1253
Publication Date (Web): March 1, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00072
Stereodivergent metallacycle-mediated cross-coupling reactions are described for the synthesis of densely functionalized vinylcyclopropanes from the union of alkynes with cyclopropenes. Strategies explored include hydroxyl-directed and nondirected ...
Barry M. Trost and Michael C. Ryan
J. Am. Chem. Soc., 2016, 138 (9), pp 2981–2984
Publication Date (Web): February 21, 2016 (Communication)
DOI: 10.1021/jacs.6b00983
Allylic chlorides prepared from commercially available trans-1,4-dichloro-2-butene were converted to trans-disubstituted 5- and 6-membered ring systems with perfect diastereoselectivity and high enantioselectivity under chiral ruthenium catalysis. These ...
Marco Pieroni, Giannamaria Annunziato, Claudia Beato, Randy Wouters, Roberto Benoni, Barbara Campanini, Thelma A. Pertinhez, Stefano Bettati, Andrea Mozzarelli, and Gabriele Costantino
J. Med. Chem., 2016, 59 (6), pp 2567–2578
Publication Date (Web): February 19, 2016 (Article)
DOI: 10.1021/acs.jmedchem.5b01775
Cysteine is a building block for several biomolecules that are crucial for living organisms. The last step of cysteine biosynthesis is catalyzed by O-acetylserine sulfydrylase (OASS), a highly conserved pyridoxal 5′-phosphate (PLP)-dependent enzyme, ...
Xiang-Zhi Zhang, Ji-Yuan Du, Yu-Hua Deng, Wen-Dao Chu, Xu Yan, Ke-Yin Yu, and Chun-An Fan
J. Org. Chem., 2016, 81 (6), pp 2598–2606
Publication Date (Web): February 18, 2016 (Note)
DOI: 10.1021/acs.joc.5b02725
A novel DBU-mediated stereoselective spirocyclopropanation of para-quinone methides with sulfonium salts has been developed on the basis of the mode involving a 1,6-conjugate addition/intramolecular dearomatizing cyclization cascade. This reaction ...
Hee Nam Lim and Guangbin Dong
Org. Lett., 2016, 18 (5), pp 1104–1107
Publication Date (Web): February 10, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00207
A general and practical catalytic method has been developed for the rapid synthesis of HCTD (heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecanes) and various new 7,12-disubstituted HCTDs from norbornadienes. Compared to the known approaches, this ...
Xiaohong Chen, Xiaoguang Liu, and Justin T. Mohr
Org. Lett., 2016, 18 (4), pp 716–719
Publication Date (Web): February 3, 2016 (Letter)
DOI: 10.1021/acs.orglett.5b03689
Carbonyl compounds bearing a γ-amino group are valuable pharmacologically active targets. Regioselective γ-C–N bond formation is achieved with simple enone substrates through controlled dienolate reactivity toward azodicarboxylate electrophiles. The ...
Ricarda Miller, Javier Carreras, Michael E. Muratore, Morgane Gaydou, Francesco Camponovo, and Antonio M. Echavarren
J. Org. Chem., 2016, 81 (5), pp 1839–1849
Publication Date (Web): February 3, 2016 (Article)
DOI: 10.1021/acs.joc.5b02607
A practical aminocyclization of 1,6-enynes with a wide variety of substituted anilines, including N-alkyl anilines, has been achived by using cationic [JohnPhosAu(MeCN)]SbF6 as a general purpose catalyst. The resulting adducts can be easily converted into ...
Anil Kumar, Subrata K. Ghosh, and John A. Gladysz
Org. Lett., 2016, 18 (4), pp 760–763
Publication Date (Web): January 28, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00023
The enantiopure salt Δ-[Co((S,S)-dpen)3]3+2Cl–B(C6F5)4– is an effective hydrogen bond donor catalyst for additions of 1,3-dicarbonyl compounds to di-tert-butyl azodicarboxylate in the presence of N-methylmorpholine (1.0:1.0:0.10) in CH3CN at 0 °C, as ...
Radhika Chopra, Kamaldeep Sharma, Manoj Kumar, and Vandana Bhalla
J. Org. Chem., 2016, 81 (3), pp 1039–1046
Publication Date (Web): January 12, 2016 (Article)
DOI: 10.1021/acs.joc.5b02495
Silver nanoparticles (AgNPs) stabilized by aggregates of derivative 4 have been used as catalyst for the construction of synthetically and biologically important [4 + 2] cycloadducts at room temperature.
Steffen Kress, Thomas Johnson, Florian Weisshar, and Mark Lautens
ACS Catal., 2016, 6 (2), pp 747–750
Publication Date (Web): December 31, 2015 (Letter)
DOI: 10.1021/acscatal.5b02387
We report the application of cyclohexa-2,5-dienols in a catalytic redox isomerization: a rhodium-catalyzed desymmetrization for the synthesis of γ,γ-disubstituted cyclohexenones. The reaction generates products which are useful intermediates in organic ...
Zhoulong Fan, Shiqi Shu, Jiabin Ni, Qizheng Yao, and Ao Zhang
ACS Catal., 2016, 6 (2), pp 769–774
Publication Date (Web): December 23, 2015 (Research Article)
DOI: 10.1021/acscatal.5b02483
Stereoselective functionalization of the adamantyl bridge methylene C(sp3)–H bonds is a rather appealing, yet challenging strategy due to the bulky and unactivated nature. Here we present a palladium-catalyzed C(sp3)–H arylation/hetereoarylation of the ...
Kaoru Usami, Yoshitomo Nagasawa, Eiji Yamaguchi, Norihiro Tada, and Akichika Itoh
Org. Lett., 2016, 18 (1), pp 8–11
Publication Date (Web): December 14, 2015 (Letter)
DOI: 10.1021/acs.orglett.5b02957
The intermolecular cyclopropanation of aromatic olefins with activated methylene compounds using iodine and visible light irradiation was described. This reaction proceeds under rare-metal-free conditions. Styrenes with various substituted groups (alkyl ...
Jomy Joseph, Preethanuj Preethalayam, K. V. Radhakrishnan, Florian Jaroschik, and Jean-Luc Vasse
Org. Lett., 2015, 17 (24), pp 6202–6205
Publication Date (Web): December 4, 2015 (Letter)
DOI: 10.1021/acs.orglett.5b03195
Zirconium hydride-catalyzed C═C double bond migration from nonconjugated to conjugated dienes is described. Applied to 1-substituted 1,4-dihydrofulvenes, the migration leads selectively to 1-substituted 1,2-dihydrofulvenes. The C═C double bond migration ...
Zhishi Ye, Kristen E. Gettys, Xingyu Shen, and Mingji Dai
Org. Lett., 2015, 17 (24), pp 6074–6077
Publication Date (Web): December 4, 2015 (Letter)
DOI: 10.1021/acs.orglett.5b03096
Novel and general copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported. ...
Taro Hamasaki, Yuka Aoyama, Junichi Kawasaki, Fumitoshi Kakiuchi, and Takuya Kochi
J. Am. Chem. Soc., 2015, 137 (51), pp 16163–16171
Publication Date (Web): December 3, 2015 (Article)
DOI: 10.1021/jacs.5b10804
Carbon–carbon bond formation at unreactive sp3-carbons in small organic molecules via chain walking was achieved for the palladium-catalyzed cycloisomerization of 1,n-dienes. Various 1,n-dienes (n = 7–14) such as those containing cyclic alkenes, acyclic ...
Daniel S. Müller and Ilan Marek
J. Am. Chem. Soc., 2015, 137 (49), pp 15414–15417
Publication Date (Web): December 1, 2015 (Communication)
DOI: 10.1021/jacs.5b11220
The enantioselective synthesis of cyclopropylzinc reagents has been achieved via a copper-catalyzed carbozincation of 3,3-disubstituted cyclopropenes with diorganozinc reagents. The obtained organozinc compounds can be easily functionalized with a broad ...
Ravindra Kumar, Hiromu Tokura, Akira Nishimura, Tadashi Mori, Yoichi Hoshimoto, Masato Ohashi, and Sensuke Ogoshi
Org. Lett., 2015, 17 (24), pp 6018–6021
Publication Date (Web): November 30, 2015 (Letter)
DOI: 10.1021/acs.orglett.5b02983
A nickel(0)/chiral N-heterocyclic carbene (NHC)-catalyzed fully intermolecular, enantioselective [2 + 2 + 2] cycloaddition of two enones and an alkyne has been developed to access enantioenriched cyclohexenes. A single diastereomer was obtained with a ...
