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A Direct Organocatalytic Entry to Selectively Protected Aldopentoses and Derivatives
Author(s) -
Grondal Christoph,
Enders Dieter
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600573
Subject(s) - chemistry , aldol reaction , thio , alkylation , carbohydrate synthesis , organocatalysis , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , carbohydrate , catalysis
The proline‐catalysed aldol reaction of 2,2‐dimethyl‐1,3‐dioxan‐5‐one with dimethoxyacetaldehyde is used as the key reaction according to the biomimetic C 3 +C n strategy for de novo carbohydrate synthesis. Based on the Whitesides inversion strategy, protected D ‐ erythro ‐pentos‐4‐ulose ( de >96 %, ee =94 %) was employed for a rapid and divergent entry to various selectively and partly orthogonal protected aldopentoses and derivatives, like amino sugars, thio sugars, deoxy sugars, 4‐ C ‐substituted (alkylated) aldopentoses and epoxy sugars.