174061-08-6Relevant academic research and scientific papers
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
Marshall, James A.,Hinkle, Kevin W.
, p. 105 - 108 (2007/10/03)
The 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.
