Stereoselective S<sub>E</sub>2‘ Additions of Enantioenriched Allylic Tin and Indium Reagents to Protected Threose and Erythrose Aldehydes:  A General Strategy for the Stereocontrolled Synthesis of Precursors to the Eight Diastereomeric Hexoses and Their Enantiomers James A. Marshall Kevin W. Hinkle 10.1021/jo951563+.s001 https://acs.figshare.com/articles/journal_contribution/Stereoselective_S_sub_E_sub_2_Additions_of_Enantioenriched_Allylic_Tin_and_Indium_Reagents_to_Protected_Threose_and_Erythrose_Aldehydes_A_General_Strategy_for_the_Stereocontrolled_Synthesis_of_Precursors_to_the_Eight_Diastereomeric_Hexoses_and_Their_Enant/3701097 The enantioenriched (∼90−95% ee) α-alkoxy allylic stannanes <i>(S)</i>- and <i>(R)</i>-<b>2.1</b> undergo <i>in situ</i> transmetallation with InCl<sub>3</sub> in EtOAc and subsequent S<sub>E</sub>2‘ addition to aldehydes to afford <i>anti</i> adducts <b>3.2a</b><b>−</b><b>d</b> stereospecifically with excellent diastereoselectivity (90:10−98:2). Additions to the protected threose and erythrose aldehydes <b>4.2</b> and <b>4.4</b> are reagent controlled, yielding the <i>anti</i> adducts <b>5.1</b>−<b>5.4</b> with high stereoselectivity. These adducts are potential precursors of differentially protected l-talose, d-allose, l-glucose, and d-mannose. 1996-01-12 00:00:00 Indium Reagents General Strategy InCl 3 Erythrose Aldehydes Diastereomeric Hexoses erythrose aldehydes 4.2 adducts 3.2 Enantioenriched Allylic Tin Stereocontrolled Synthesis Protected Threose