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A Catalytic Asymmetric Chlorocyclization of Unsaturated Amides


  • We acknowledge the ACS PRF (No. 47272-AC) and the NSF (No. CHE-0957462) for generous funding. We also thank Adam Ryske for assistance in the synthesis of some of the substrates in Table 3.


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The asymmetric chlorocyclization of unsaturated amides catalyzed by (DHQD)2PHAL yields oxazoline and dihydrooxazine derivatives (see scheme). The reaction is operationally simple and employs 1–2 mol % of the commercially available (DHQD)2PHAL (hydroquinidine 1,4-phthalazinediyl diether) catalyst. Different substitution patterns of the olefin as well as aromatic and aliphatic olefin substituents are well tolerated. DCDPH=N,N-dichloro-5,5-diphenylhydantoin.