Enantioselective cascade radical addition-cyclization of oxime ethers

Synlett

Volumn , Issue 12, 2007, Pages 1885-1888

  Miyabe, Hideto ^a,b   Toyoda, Akira ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b HYOGO COLLEGE OF MEDICINE   (Japan)

Author keywords

Cascade; Enantioselective; Lewis acid; Oxime ether; Radical

Indexed keywords

OXIME DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; ENANTIOSELECTIVITY;

EID: 34547632200     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984530     Document Type: Article

References (48)

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44. 9 The relative configuration of the trans and cis diastereomers was determined by NOESY experiments.
45. 3B in hexane for this experiment.
46. 2Zn or 9-BBN as a radical initiator, no reaction occurred.
47. 4 and concentrated at reduced pressure. Purification of the residue by column chromatography (hexane-EtOAc, 2:1) afforded product 3a (32 mg, 70%) as a mixture of cis and trans isomers which were separated by column chromatography (hexane-EtOAc, 4:1). The enantioselectivity of products was determined by HPLC using AD-H column.
48. 3: 383.2335; found: 383.2342.