ChemInform Abstract: Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to 2,3‐Di‐O‐isopropylidene‐D‐glyceraldehyde Nitrones. Synthesis of L‐Isoxazolidinyl Nucleosides.

Abstract

Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to 2,3-Di-O-isopropylidene-D-glyceraldehyde Nitrones.Synthesis of L-Isoxazolidinyl Nucleosides.-Under optimized conditions, the BF 3etherate promoted addition of the silyl ketene acetal (II) to a D-glyceraldehyde derived nitrone (I) gives the isoxazolidinone (III) in high yield and stereoselectivity. The anti product is readily converted to key intermediates (VIII) and (IX) of L-isoxazolidinyl nucleosides such as (X) and (XI). -(MERINO, PEDRO; DEL ALAMO, EVA M.; BONA, MAITE; FRANCO, SANTIAGO; MERCHAN, FRANCISCO L.; TEJERO, TOMAS; VIECELI, ODILE; Tetrahedron Lett. 41 (2000) 48, 9239-9243; Dep. Quim. Org., ICMA, Fac. Cienc., Univ. Zaragoza,