Journal
ORGANIC LETTERS
Volume 15, Issue 6, Pages 1342-1345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400252p
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A practical, enantioselective synthesis of cis-2,5-disubstituted pyrrolidine is described. Application of an enzymatic DKR reduction of a keto ester, which is easily accessed through a novel intramolecular N -> C benzoyl migration, yields syn-1,2-amino alcohol in >99% ee and >99:1 dr. Subsequent hydrogenation of cyclic imine affords the cis-pyrrolidine in high diastereoselectivity. By integrating biotechnology into organic synthesis and isolating only three intermediates over 11 steps, the core scaffold of beta(3)-AR agonists is synthesized In 38% overall yield.
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