Insertion reactions of macrocyclic rhodium carbenoids: a novel method for the synthesis of cryptands

Tetrahedron Letters

Volumn 48, Issue 38, 2007, Pages 6821-6824

  Muthusamy, Sengodagounder ^a   Gnanaprakasam, Boopathy ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

Carbenoids; Cryptands; Diazo ketones; Macrocyclic lactones; O H insertion; Rhodium(II) acetate

Indexed keywords

ALCOHOL DERIVATIVE; CARBENOID; CARBONYL DERIVATIVE; HYDROXYL GROUP; MACROCYCLIC COMPOUND; RHODIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 34548021253     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.035     Document Type: Article

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32. General procedure for the O-H insertion reaction: Method A for the synthesis of dilactones 2: A mixture of macrocyclic diazocarbonyl compound 1b (0.5 mmol) and the appropriate alcohol (0.7 mmol) was taken in dry DCM (50 mL) under an argon atmosphere. To the above solution, 2 mol % of rhodium(II) acetate dimer catalyst was added and the mixture was stirred at reflux for 2 h. The progress of the reaction was monitored by TLC. The solvent was removed under reduced pressure and the resulting residue purified using 100-200 mesh silica gel column chromatography (hexane/EtOAc or EtOAc/MeOH) to afford the respective substituted macrocyclic dilactone 2.
33. Method B for the synthesis of dilactones 3: To an oven-dried flask, the appropriate alcohol (0.5 mmol) and 2 mol % of rhodium(II) acetate in dry benzene or DCM (100 mL) were added under an inert atmosphere and the mixture was heated at reflux. To the above refluxing mixture, macrocyclic diazocarbonyl compound 1b (1.2 mmol) in dry benzene or DCM was added slowly over 1 h using a syringe pump and reflux for 6 h. The progress of the reaction was monitored by TLC. The solvent was removed under reduced pressure and the resulting residue purified using 100-200 mesh silica gel column chromatography (hexane/EtOAc) to afford the respective double O-H insertion products 3. The macrocyclic tetralactones 4 were synthesized by the reaction of the bis-diazocarbonyl compounds 1d-h (0.5 mmol) with an excess of the respective alcohol (1.5 mmol) in the presence of rhodium(II) acetate in dry benzene or DCM (100 mL) under reflux conditions.
34. Method C for the synthesis of cryptands 5: A mixture of bis-macrocyclic diazocarbonyl compound 1d,e,g,h (0.5 mmol) and the appropriate dihydroxy compound (0.5 mmol) was taken in dry DCM (50 mL) under an argon atmosphere. To the above solution, 2 mol % of rhodium(II) acetate dimer catalyst was added and the reaction stirred at reflux for 6 h. The progress of the reaction was monitored by TLC. The solvent was removed under reduced pressure and the resulting residue purified using 100-200 mesh silica gel column chromatography (hexane/EtOAc or EtOAc) to afford the respective cryptands 5.
35. +: 597.2887, found 597.2861.