Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram |
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Authors: | Abhimanyu S Paraskar |
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Institution: | Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India |
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Abstract: | Sodium borohydride in combination with a catalytic amount of CoCl2 has been found to be an excellent catalytic system in reductive cyclizations of suitably substituted azido and cyano groups of α,β-unsaturated esters to afford γ and δ-lactams in high yields. The process has been demonstrated for the enantioselective synthesis of (R)-baclofen, (R)-rolipram, and (R)-4-fluorophenylpiperidinone, a key intermediate for (−)-paroxetine. |
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Keywords: | Asymmetric synthesis Reduction γ and δ-Lactams Cobalt chloride Sodium borohydride |
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