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