A Complementary Toolbox of Iterative Methods for the Stereoselective Synthesis of Heteroatom-Rich Motives from C (1) -Building Blocks

作者：Kirupakaran Sujenth; Korth Hans Gert; Hirschhaeuser Christoph

来源：Synthesis (Germany), 2018, 50(12): 2307-2322.

DOI：10.1055/s-0036-1591996

<jats:p>The ability to assemble organic molecules one carbon atom at a time has been a long-held dream for chemists. Modern boronate homologations with chiral carbenoids allow for the assembly-line synthesis of long chiral alkyl chains with excellent control over individual stereocenters. Nevertheless, heteroatom rich motives present a serious synthetic challenge to this approach. Interestingly, older methods based on substrate-controlled homologations of chiral boronic esters or umpolung of a carbonyl nucleophile can offer complementary solutions. A combination of these approaches might thus extend the range of possible targets currently within grasp of a C1-based synthesis. Link to video abstract: https://www.youtube.com/watch?v=PH_HBrqQwtg .</jats:p><jats:p>1 Introduction</jats:p><jats:p>2 Substrate Control: Stereoselective Addition of d1-Reagents to Aldehydes­</jats:p><jats:p>3 Stereocontrol by Chiral Auxiliary/Director: The Matteson Boronate Homologation</jats:p><jats:p>4 Reagent Control: Moving Chiral Information to the Carbenoid</jats:p><jats:p>5 Conclusions and Outlook</jats:p>

• 出版日期2018-6