Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 18, Pages 9076-9084Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4012656
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Funding
- CSIR-SRF
- DST
- CSIR Network Project on Catalysis
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Chiral polymeric Co(III) salen complexes with chiral ((R)/(S)-BINOL, diethyl tartrate) and achiral (piper- azine and trigol) linkers with varying stereogenic centers were synthesized for the first time and used as catalysts for aminolytic kinetic resolution (AKR) of a variety of terminal epoxides and glycidyl ethers to get enantio-pure epoxides (ee, 99%) and N-protected beta-amino alcohols (ee, 99%) with quantitative yield in 16 h at RT under optimized reaction conditions. This protocol was also used for the synthesis of two enantiomerically pure drug molecules (R)-Naftopidil (alpha(1)-blocker) and (S)-Propranolol (beta-blocker) as a key step via AKR of single racemic naphthylglycidyl ether with Boc-protected isoproylamine with 100% epoxide utilization at 1 g level. The catalyst 1 was successfully recycled for a number of times.
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