Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone.
The HKR of racemic syn- or anti- alkoxy- and azido epoxides catalyzed by Co(salen) complex affords a practical access to a series of enantioenriched syn- or anti- alkoxy- and azido epoxides and the corresponding 1,2-diols. This strategy has been successfully employed in the concise, enantioselective synthesis of bioactive molecules such as (S,S)-reboxetine and (+)-epi-cytoxazone.
Chemical Engineering and Process Development Division, National Chemical Laboratoty, Pashan Road, Pune, 411008, India.
R Santhosh
RS
Reddy
Pandurang V
PV
Chouthaiwale
Gurunath
G
Suryavanshi
Vilas B
VB
Chavan
Arumugam
A
Sudalai
D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D000077593:Reboxetine; D013237:Stereoisomerism
D000928:Antidepressive Agents; D056831:Coordination Complexes; D004852:Epoxy Compounds; D005029:Ethylenediamines; D009025:Morpholines; D010080:Oxazoles; D003035:Cobalt; C117832:cytoxazone; C011452:disalicylaldehyde ethylenediamine; D000077593:Reboxetine