Chemical Communications

Enantiomerically enriched [2-2 H]-isopentenyl alcohol from (E)-2-methylbut-2-ene-1, 4-diol by an asymmetric retro-ene reaction

JL Giner, D Arigoni

文献索引：Giner, Jose-Luis; Arigoni, Duilio Chemical Communications, 2002 , # 13 p. 1388 - 1389

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摘要

A stereospecific transfer of the acetal H-atom to the 2-position of isopentenyl alcohol could be achieved, in principle, by pyrolysis of a chiral acetal such as a glycoside. In order to test this possibility, the 1-tetraacetyl-β-D-glucoside of (E)-2-methylbut-2-ene-1,4-diol (2) and its silyl derivative 4 were synthesized and subjected to pyrolysis. ... Fig. 1 Synthesis of and pyrolysis reaction of (E)-4-hydroxy-2-methylbut-2-enyl 1-tetra-O-acetyl-β-D-glucopyranoside (2) and its silyl ...