C-N Ring Construction: The Zakarian Synthesis of (-)-Rhazinilam

William D. Wulff of Michigan State University developed (J. Am. Chem. Soc. 2010, 132, 13100; Org. Lett. 2010, 12, 4908) a general enantio- and diastereocontrolled route from an imine 1 to the aziridine 3. Craig W. Lindsley of Vanderbilt University established (Org. Lett. 2010, 12, 3276) a complementary approach (not illustrated). Joseph P. Konopelski of the University of California, Santa Cruz, designed (J. Am. Chem. Soc. 2010, 132, 11379) a practical and inexpensive flow apparatus for the cyclization of 4 to the β-lactam 5. Manas K. Ghorai of the Indian Institute of Technology, Kanpur, showed (J. Org. Chem. 2010, 75, 6173) that an aziridine 6 could be opened with malonate to give the γ-lactam 8. John P. Wolfe of the University of Michigan devised (J. Am. Chem. Soc. 2010, 132, 12157) a Pd catalyst for the enantioselective cyclization of 9 to 11. Sherry R. Chemler of the State University of New York at Buffalo observed (Angew. Chem. Int. Ed. 2010, 49, 6365) that the cyclization of 12 to 14 proceeded with high diastereoselectivity. Glenn M. Sammis of the University of British Columbia devised (Synlett 2010, 3035) conditions for the radical cyclization of 15 to 16. Jeffrey S. Johnson of the University of North Carolina observed (J. Am. Chem. Soc. 2010, 132, 9688) that the opening of racemic 17 with 18 could be effected with high ee. The residual 17 was highly enriched in the nonreactive enantiomer. Kevin D. Moeller of Washington University found (Org. Lett . 2010, 12, 5174) that the n -BuLi catalyzed cyclization of 20 set the quaternary center of 21 with high relative control. Yujiro Hayashi of the Tokyo University of Science, using the diphenyl prolinol TMS ether that he developed as an organocatalyst, designed (Org. Lett. 2010, 12, 4588) the sequential four-component coupling of 22, 23, benzaldehyde imine, and allyl silane to give 24 with high relative and absolute stereocontrol. Derrick L. J. Clive of the University of Alberta showed (J. Org. Chem. 2010, 75, 5223) that 25, prepared in enantiomerically pure form from serine, participated smoothly in the Claisen rearrangement, to deliver 27.