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Synlett 2009(11): 1861-1862  
DOI: 10.1055/s-0029-1217374
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Glyceraldehyde Acetonide - Recent Applications of this Chiron in Organic Synthesis

Evanoel Crizanto de Lima*
Laboratório de Química Bioorgânica (LQB), NPPN, Bl H, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, ­Cidade Universitária, CEP: 21941-590, Rio de Janeiro, Brazil
e-Mail: evanoel.crizanto@gmail.com;
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Publication History

Publication Date:
16 June 2009 (online)

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Introduction

Glyceraldehyde acetonide (2,3-O-isopropylidene-d-gly­ceraldehyde, 1) it is a well-known chiron which has been used in organic synthesis for multiple purposes. [¹] It has been applied on the synthesis of a β-adrenergic antagonist, [²] on multicomponent reaction in the synthesis of ­nakadomarin A precursor, [³] and reacts with several organometallics to afford chiral alcohols used as precursors in total syntheses. [4-7] Its R isomer is easily prepared from selective protection and oxidative cleavage of ­in­expensive and available commercially d-mannitol (Scheme  [¹] ) [8] and its enantiomer can be obtained from vitamin C. [9] The present Spotlight emphasises recent applications of this chiron in organic synthesis in its R and S enantiomeric forms.

Scheme 1