Organic Syntheses
Volume 96
Organic Syntheses (Band Nr. 96)
1. Auflage Mai 2020
656 Seiten, Hardcover
Monographie
ISBN:
978-1-119-70776-9
John Wiley & Sons
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Discussion Addendum for: 4-Nonylbenzoic Acid 1
Alois Fürstner
Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix 16
Junting Chen and Tobias Ritter
Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 36
Yuki Kawashima, Takayuki Furukawa, Naoto Chatani and Mamoru Tobisu
Discussion Addendum for: Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to alpha,ß-Unsaturated Esters: Asymmetric Synthesis of (S)-ß-Leucine 53
Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, and James E. Thomson
Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates 66
Mi-Na Zhao and Zheng-Hui Guan
Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2- (2-acetylphenyl)acetate 80
Austin C. Wright and Brian M. Stoltz
Discussion Addendum for: Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate 98
Mizzanoor Rahaman and M. Mahmun Hossain
Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate 110
Aslam C. Shaikh and Ohyun Kwon
Discussion Addendum for: Protection of Alcohols using 2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-methyl Propanoate 124
Harvey F. Fulo, Philip A. Albiniak, and Gregory B. Dudley
Synthesis of 4-Methylbenzoate(2',4',6'-trimethoxy-phenyl)iodonium Tosylate 137
Thomas L. Seidl, Aaron Moment, Charles Orella, Thomas Vickery, and David R. Stuart
Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes 150
Chris Nottingham, Verity Barber, and Guy C. Lloyd-Jones
Discussion Addendum for: Preparation of Enantioenriched Homoallylic Primary Amines 179
Miguel Yus
Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide 195
Cédric Theunissen, Pierre Thilmany, Mounsef Lahboubi, Nicolas Blanchard, and Gwilherm Evano
Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate 214
Aslam C. Shaikh and Ohuyn Kwon
Discussion Addendum for: Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines 232
Miguel Yus
Synthesis of Chiral Diamine Ligands for Nickel-catalyzed Asymmetric Cross-couplings of Alkylchloroboronate Esters with Alkylzincs: 1R,2R)-N,N'-Dimethyl-1,2-bis(2-methylphenyl)-1,2-diaminoethane 245
Yusuke Masuda and Gregory C. Fu
Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d] thiophenium triflate 258
Bernd Waldecker, Kevin Kafuta, and Manuel Alcarazo
Three-Step Synthesis of 2-(Diiodomethyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane from Dichloromethane 277
Morgane Sayes, Guillaume Benoit, and André B. Charette
Discussion Addendum for: Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[epsilon-caprolactamate] of tert-Butyldimethylsilylprotected trans-Dehydroandrosterone 300
Yong-Liang Su, Luca De Angelis and Michael P. Doyle
Preparation of (R)-3-(3,5-Bistrifluoromethylphenyl)-1,1'-bi-2-naphthol 312
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Catalytic Enantioselective Addition of an In-Situ Prepared Aryltitanium Reagent to p-Chloroacetophenone: (R)-(+)-1-(4-Chlorophenyl)-1-m-tolylethanol 333
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Stereoselective Synthesis of (R)-((R)-1-Phenyl-2,2,2-trichloroethyl)-2-(2-bromophenyl)aziridine-1-carboxylate 351
Hélène Lebel and Henri Piras
Discussion Addendum for: Preparation of (R,R)-1,2:4,5-Diepoxypentane 361
Nicholas Sizemore and Scott D. Rychnovsky
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine 382
Scott E. Denmark and Pavel Ryabchuk
Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification 400
Scott E. Denmark, Pavel Ryabchuk, Hyung Min Chi, and Anastassia Matviitsuk
anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide 418
Trevor V. Nykaza, Julian C. Cooper, and Alexander T. Radosevich
Facile Reduction of Amides Using Nickel Catalysis: Reduction of 12-Aminododecanolactam 436
Bryan J. Simmons, Melissa Ramirez, and Neil K. Garg
Preparation of 2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile 455
Saskia M. Engle, Takisha R. Kirkner, and Christopher B. Kelly
Discussion Addendum for: Fluorobis(phenylsulfonyl)methane (FBSM) 474
Xanath Ispizua-Rodriguez, Vinayak Krishnamurti, Mathew Coe, and G. K. Surya Prakash
Synthesis of 5-Hydroxy-4-methoxy-2-methylpyrylium Trifluoromethanesulfonate from Kojic Acid 494
Nana B. Agyemang and Ryan P. Murelli
Iridium-Catalyzed Reductive Coupling of Grignard Reagents and Tertiary Amides 511
Pablo Gabriel, Lan-Gui Xie, and Darren J. Dixon
Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride 528
Kyle M. Lambert, Austin W. Medley, Amy C. Jackson, Lauren E. Markham, and John L. Wood
Synthesis of 8-Hydroxygeraniol 586
Francesca M. Ippoliti, Joyann S. Barber, and Neil K. Garg
Alois Fürstner
Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix 16
Junting Chen and Tobias Ritter
Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 36
Yuki Kawashima, Takayuki Furukawa, Naoto Chatani and Mamoru Tobisu
Discussion Addendum for: Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to alpha,ß-Unsaturated Esters: Asymmetric Synthesis of (S)-ß-Leucine 53
Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, and James E. Thomson
Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates 66
Mi-Na Zhao and Zheng-Hui Guan
Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2- (2-acetylphenyl)acetate 80
Austin C. Wright and Brian M. Stoltz
Discussion Addendum for: Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate 98
Mizzanoor Rahaman and M. Mahmun Hossain
Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate 110
Aslam C. Shaikh and Ohyun Kwon
Discussion Addendum for: Protection of Alcohols using 2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-methyl Propanoate 124
Harvey F. Fulo, Philip A. Albiniak, and Gregory B. Dudley
Synthesis of 4-Methylbenzoate(2',4',6'-trimethoxy-phenyl)iodonium Tosylate 137
Thomas L. Seidl, Aaron Moment, Charles Orella, Thomas Vickery, and David R. Stuart
Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes 150
Chris Nottingham, Verity Barber, and Guy C. Lloyd-Jones
Discussion Addendum for: Preparation of Enantioenriched Homoallylic Primary Amines 179
Miguel Yus
Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide 195
Cédric Theunissen, Pierre Thilmany, Mounsef Lahboubi, Nicolas Blanchard, and Gwilherm Evano
Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate 214
Aslam C. Shaikh and Ohuyn Kwon
Discussion Addendum for: Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines 232
Miguel Yus
Synthesis of Chiral Diamine Ligands for Nickel-catalyzed Asymmetric Cross-couplings of Alkylchloroboronate Esters with Alkylzincs: 1R,2R)-N,N'-Dimethyl-1,2-bis(2-methylphenyl)-1,2-diaminoethane 245
Yusuke Masuda and Gregory C. Fu
Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d] thiophenium triflate 258
Bernd Waldecker, Kevin Kafuta, and Manuel Alcarazo
Three-Step Synthesis of 2-(Diiodomethyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane from Dichloromethane 277
Morgane Sayes, Guillaume Benoit, and André B. Charette
Discussion Addendum for: Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[epsilon-caprolactamate] of tert-Butyldimethylsilylprotected trans-Dehydroandrosterone 300
Yong-Liang Su, Luca De Angelis and Michael P. Doyle
Preparation of (R)-3-(3,5-Bistrifluoromethylphenyl)-1,1'-bi-2-naphthol 312
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Catalytic Enantioselective Addition of an In-Situ Prepared Aryltitanium Reagent to p-Chloroacetophenone: (R)-(+)-1-(4-Chlorophenyl)-1-m-tolylethanol 333
Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada
Stereoselective Synthesis of (R)-((R)-1-Phenyl-2,2,2-trichloroethyl)-2-(2-bromophenyl)aziridine-1-carboxylate 351
Hélène Lebel and Henri Piras
Discussion Addendum for: Preparation of (R,R)-1,2:4,5-Diepoxypentane 361
Nicholas Sizemore and Scott D. Rychnovsky
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine 382
Scott E. Denmark and Pavel Ryabchuk
Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification 400
Scott E. Denmark, Pavel Ryabchuk, Hyung Min Chi, and Anastassia Matviitsuk
anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide 418
Trevor V. Nykaza, Julian C. Cooper, and Alexander T. Radosevich
Facile Reduction of Amides Using Nickel Catalysis: Reduction of 12-Aminododecanolactam 436
Bryan J. Simmons, Melissa Ramirez, and Neil K. Garg
Preparation of 2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile 455
Saskia M. Engle, Takisha R. Kirkner, and Christopher B. Kelly
Discussion Addendum for: Fluorobis(phenylsulfonyl)methane (FBSM) 474
Xanath Ispizua-Rodriguez, Vinayak Krishnamurti, Mathew Coe, and G. K. Surya Prakash
Synthesis of 5-Hydroxy-4-methoxy-2-methylpyrylium Trifluoromethanesulfonate from Kojic Acid 494
Nana B. Agyemang and Ryan P. Murelli
Iridium-Catalyzed Reductive Coupling of Grignard Reagents and Tertiary Amides 511
Pablo Gabriel, Lan-Gui Xie, and Darren J. Dixon
Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride 528
Kyle M. Lambert, Austin W. Medley, Amy C. Jackson, Lauren E. Markham, and John L. Wood
Synthesis of 8-Hydroxygeraniol 586
Francesca M. Ippoliti, Joyann S. Barber, and Neil K. Garg
