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(+)‐( R , Z )‐5‐Muscenone and (−)‐( R )‐Muscone by Enantioselective Aldol Reaction and Grob Fragmentation
Author(s) -
Fehr Charles,
Buzas Andrea K.,
Knopff Oliver,
de Saint Laumer JeanYves
Publication year - 2010
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.200902774
Subject(s) - enantioselective synthesis , aldol reaction , chemistry , stereochemistry , fragmentation (computing) , reagent , substrate (aquarium) , enantiomeric excess , organic chemistry , catalysis , biology , ecology
(+)‐( R , Z )‐5‐Muscenone (( R )‐ 1 ) was synthesized by an enantioselective aldol reaction, catalyzed by new ephedrine‐type Ti reagents (up to 70 % enantiomeric excess). Substrate‐directed diastereoselective reduction of the aldol product and Grob fragmentation of the tosylate of the resultant 1,3‐diol afforded (+)‐ 1 . This approach also gave access to (−)‐( R , E )‐5‐muscenone and (−)‐( R )‐muscone.
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