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Stereoselective SE2‘ 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
journal contribution
posted on 1996-01-12, 00:00 authored by James A. Marshall, Kevin W. HinkleThe enantioenriched (∼90−95% ee) α-alkoxy
allylic stannanes (S)- and (R)-2.1
undergo in situ
transmetallation with InCl3 in EtOAc and subsequent
SE2‘ addition to aldehydes to afford
anti
adducts 3.2a−d stereospecifically
with excellent diastereoselectivity (90:10−98:2). Additions
to
the protected threose and erythrose aldehydes 4.2 and
4.4 are reagent controlled, yielding the
anti
adducts 5.1−5.4 with high stereoselectivity.
These adducts are potential precursors of
differentially
protected l-talose, d-allose,
l-glucose, and d-mannose.