Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom