Radical [3 + 2] annulation of N-allyl-N-chlorotosylamide with alkenes via atom-transfer process

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2709-2711

  Tsuritani, Takayuki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 0000013031     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016310j     Document Type: Article

References (37)

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34. The use of THF or ether as a reaction solvent decreased the yields of the cyclization products. The reaction in water provided only the reduction product (N-allyltosytamide).
35. General Procedure. A solution of triethylborane (0.05 mL, 1.0 M hexane solution, 0.05 mmol) was added dropwise to a solution of chlorotosylamide 1d (123 mg, 0.5 mmol) and styrene (0.11 mL, 1.0 mmol) in benzene (1.5 mL) at room temperature. After the mixture was stirred for 3 h, solvent was removed under reduced pressure. Purification of the residual oil by chromatography afforded 3-chloromethyl-4-phenyl-1-tosylpyrrolidine (168 mg, 0.48 mmol) in 96% yield.
36. Typically, 10-20 equiv of alkenyl partners were employed.
37. The reaction of 1d with cyclohexene or 5-dodecene afforded N-allyltosylamide in quantitative yield. The rate of the radical addition to internal alkenes should be slow, and the abstraction of allylic hydrogen would be predominant.