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Monday, March 17, 2014
Allison K. Griffith and Tristan H. Lambert
Columbia University


The α-C-H functionalization of piperidine catalyzed by tantalum complex 1 to produce amine 2 was developed (Org. Lett. 2013, 15, 2182. ) by Laurel L. Schafer at the University of British Columbia. An asymmetric diamination of diene 3 with diaziridine reagent 4 under palladium catalysis to furnish cyclic sulfamide 5 was developed (Org. Lett. 2013, 15, 796. ) by Yian Shi at Colorado State University. Enantioenriched β-fluoropiperdine 8 was prepared (Angew. Chem. Int. Ed. 2013, 52, 2469. ) via aminofluorocyclization with hypervalent iodide 7, as reported by Cristina Nevado at the University of Zürich. Erick M. Carreira at ETH Zürich disclosed (J. Am. Chem. Soc. 2013, 135, 6814. ) a ruthenium-catalyzed hydrocarbamoylation of allylic formamide 9 to yield pyrrolidone 10.

Hans-Günther Schmalz at the University of Köln disclosed (Angew. Chem. Int. Ed. 2013, 52, 1576. ) an asymmetric hydrocyanation of styrene with Ni(cod)2 and phosphine-phosphite ligand 12 to yield exclusively the branched cyanide 13. A similar transformation of styrene to the hydroxycarbonylated product 15 was catalyzed (Chem. Commun. 2013, 49, 3306. ) by palladium complex 14, as reported by Matthew L. Clarke at the University of St Andrews.

Feng-Ling Qing at the Chinese Academy of Sciences found (Angew. Chem. Int. Ed. 2013, 52, 2198. ) that the hydrotrifluoromethylation of unactivated alkene 16 was catalyzed by silver nitrate. The same transformation was also reported (J. Am. Chem. Soc. 2013, 135, 2505. ) by Veronique Gouverneur at the University of Oxford using a ruthenium photocatalyst and the Umemoto reagent 18.

Clark R. Landis at the University of Wisconsin-Madison reported (Angew. Chem. Int. Ed. 2013, 52, 1564. ) a one-pot asymmetric hydroformylation and Wittig olefination to transform alkene 19 into γ-chiral α,β-unsaturated carbonyl compound 20. Debabrata Mati at the Indian Institute of Technology Bombay found (J. Am. Chem. Soc. 2013, 135, 3355. ) that alkene 22 could be nitrated stereoselectively with silver nitrite and TEMPO to form alkene 23.

Damian W. Young at the Broad Institute disclosed (Org. Lett. 2013, 15, 1218. ) that a macrocyclic vinylsiloxane 24, which was synthesized via an E-selective ring closing metathesis reaction, could be functionalized to make either E- or Z-alkenes, 25 and 26.

A ruthenium catalyst 28 exhibiting Z-selectivity for the homodimerization of alkene 27 was disclosed (J. Am. Chem. Soc. 2013, 135, 1276. ) by Robert H. Grubbs at Caltech. Meanwhile, a Z-selective cross metathesis of vinyl-B(pin) (30) and alkene 32 with a molybdenum catalyst 31 was disclosed (J. Am. Chem. Soc. 2013, 135, 6026. ) by Amir H. Hoveyda at Boston College.

A. K. Griffith, T. H. Lambert, Org. Chem. Highlights 2014, March 17.