Synthesis of medium-sized cyclic γ-haloketones by radical mediated ring-opening reaction of Lewis acid catalyzed (2+2)-cycloaddition products

Tetrahedron Letters

Volumn 46, Issue 6, 2005, Pages 1005-1008

  Takasu, Kiyosei ^a   Nagao, Satoshi ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

(2+2) Cycloaddition; Alkoxyl radicals; Cyclobutanols; Medium sized cycloalkanones; Ring opening reaction

Indexed keywords

ALKANONE; ETHER; HALOKETONE; LEWIS ACID;

ARTICLE; CATALYSIS; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 12344321513     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.024     Document Type: Article

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17. 4 and concentrated. The residue was purified by silica gel PTLC (AcOEt/hexane = 1:9) to give trans-6a (10 mg, 32%) and cis-6a (10 mg, 32%)
18. 9): 463.0590; found: 463.0584; Selected NOEs of trans-6a and cis-6a were shown in the following chart
19. 2 (18 mg, 69 μmol) in cyclohexane/benzene (3 mL/0.3 mL) was maintained at 45°C for 30 min with ultrasonic irradiation. Work-up and purification were carried out as the similar manner as above to give 6a (20 mg, 74%) as a mixture of diastereomers
20. Procedure for ring-opening reaction under NIS-CuI conditions: A mixture of 1a (17 mg, 44 μmol), NIS (12 mg, 52 μmol) and CuI (0.9 mg, 4.7 μmol) in cyclohexane (2.9 mL) was refluxed for 3.5 h. Work-up and purification were carried out as the similar manner as above to give 6a (19 mg, 84%) as a mixture of diastereomers