Timothy Ramadhar - Allylation of Imines and Their Derivatives with Organoboron Reagents: Stereocontrolled Synthesis of Homoallylic Amines

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  Publication Details (including relevant citation   information):

  Timothy R. Ramadhar, Robert A. Batey. Synthesis,   2011, 1321-1346.


  Homoallylic amines serve as important precursors for the   synthesis of a variety of natural products and pharmaceutically   relevant compounds. One widely used strategy for homoallylic   amine synthesis is the addition of allylic metal or metalloid   derivatives to imines or related functional groups. The use of   allylic boron compounds for these reactions has emerged as an   important synthetic approach, providing a robust and   chemoselective method for efficient and stereocontrolled access   to various homoallylic amines. In this review, a comprehensive   and critical analysis of imine allylboration and crotylboration   methods using organoborane, organoboronate and potassium   organotrifluoroborate reagents is provided. These approaches   include direct methods that accomplish diastereo- or   enantiocontrolled addition of the organoboron species.   Additionally, organoboron-based transition-metal-catalyzed   allylation of imines and their respective surrogates using   copper, indium, iridium, palladium or zinc catalysis is   discussed. Finally, coverage on the use of allenyl- and   propargylboron compounds and their application for the synthesis   of homopropargylic and homoallenyl amines is provided.

  Address (URL): http://dx.doi.org/10.1055/s-0030-1258434