Construction of Alkylated Stereogenic Centers
Andreas Pfaltz of the University of Basel and Keisuke Suzuki of Tokyo Institute of Technology showed (Angew. Chem. Int. Ed. 2010, 49, 881. ) that the iodohydrin of 1 did not interfere with the enantioselective hydrogenation. J. R. Falck of UT Southwestern developed (J. Am. Chem. Soc. 2010, 132, 2524. ) a procedure for the coupling of arene boronic acids with a cyano triflate 3, readily available in high ee from the corresponding aldehyde. Anita R. Maguire of University College Cork devised (J. Am. Chem. Soc. 2010, 132, 1184. ) a Cu catalyst for the enantioselective C-H insertion cyclization of 5 to 6. Jin-Quan Yu of Scripps/La Jolla established (J. Am. Chem. Soc. 2010, 132, 460. ) a complementary enantioselective C-H functionalization protocol, converting the prochiral 7 into 8 in high ee.
Xumu Zhang of Rutgers effected (Angew. Chem. Int. Ed. 2010, 49, 4047. ) enantioselective branching hydroformylation of 9 to give 10. T. V. RajanBabu of Ohio State University established (J. Am. Chem. Soc. 2010, 132, 3295. ) the enantioselective hydrovinylation of a diene 11 to the diene 12. Gregory C. Fu extended (J. Am. Chem. Soc. 2010, 132, 1264, , 5010, ) Ni-mediated cross-coupling, both with alkenyl and aryl nucleophiles, to the racemic bromoketone 13.
Hyeung-geun Park and Sang-sup Jew of Seoul National University used (Org. Lett. 2010, 12, 2826. ) their asymmetric phase transfer protocol to effect the enantioselective alkylation of the amide 15. Kyung Woon Jung of the University of Southern California showed (J. Org. Chem. 2010, 75, 95. ) that the oxidative Pd-mediated Heck coupling of arene boronic acids to 17 could be effected in high ee. Nicolai Cramer of ETH Zurich observed (J. Am. Chem. Soc. 2010, 132, 5340. ) high enantioinduction in the cleavage of the prochiral cyclobutanol 19.
Alexandre Alexakis of the University of Geneva achieved (Org. Lett. 2010, 12, 1988. ) the long-sought goal of efficient enantioselective conjugate addition of a Grignard reagent to an unsaturated aldehyde 21. Professor Alexakis also (Org. Lett. 2010, 12, 2770. ) established conditions for enantioselective conjugate addition to a nitrodiene 23. This procedure worked equally well for β-alkynyl nitroalkenes.
Jun-An Ma of Tianjin University used (J. Org. Chem. 2010, 75, 1402. ) organocatalysis to effect the conjugate addition of a variety of ketones, including acetone, to the nitrodiene 25. Again, β-alkynyl nitroalkenes worked well. Shu Kobayashi of the University of Tokyo observed (J. Am. Chem. Soc. 2010, 132, 7890. ) that the chiral environment around the catalyst was sufficient to control the absolute configuration of protonation after conjugate addition to 27.