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The Tandem Ring‐Closing Metathesis–Isomerization Approach to 6‐Deoxyglycals
Author(s) -
Schmidt Bernd,
Biernat Anne
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800567
Subject(s) - isomerization , chemistry , tandem , ring (chemistry) , metathesis , dimer , ring closing metathesis , disaccharide , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , polymerization , materials science , polymer , composite material
Protected 3,6‐dideoxyglycals have been synthesized de novo as single isomers starting from ethyl lactate by using the tandem RCM–isomerization reaction as the key step. Different relative configurations become accessible by addition of vinyl‐ or allyl–metal compounds to protected lactaldehydes under Cram‐chelate or Felkin–Anh control. The concept is exemplified for glycals of L ‐rhodinose and L ‐amicetose, as well as for ring‐expanded non‐natural analogues thereof. This novel approach to glycals is also applicable to the synthesis of disaccharide glycals via a reiterative strategy, as exemplified for the dimer of L ‐rhodinose and its non‐natural ring expanded analogue.