Stereochemistry of the Addition of Organometallic Reagents to Methyl 2,3- O -Isopropylidene-β-D- ribo -pentodialdo-1,4-furanose
1986; Taylor & Francis; Volume: 5; Issue: 2 Linguagem: Inglês
10.1080/07328308608062965
ISSN1532-2327
AutoresF. Leslie Boyd, David C. Baker,
Tópico(s)Synthesis of Organic Compounds
ResumoAbstract Methyl 2, 3-O- isopropylidene-β-D-ribo-pen tod ialdo-1,4-furanoside, upon reaction with either methyl lithium or methyImagnesium iodide/ gave a ca. 2-3:1 mixture of β-D-allo to α-L-talo adducts. Reaction with 2-lithio-l,3-d ithiane gave much improved stereoselectivity, in line with either the Cram or Felkin model, to give the dithianyl adducts in a ratio of 97:3 of β-D-allo to α-talo isomers.
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