Diels-Alder reactions of masked o-benzoquinones with electron-rich dienophiles. Highly regio- and stereoselective synthesis of bicyclo [2.2.2]octenone derivatives

Synlett

Volumn , Issue 3, 2000, Pages 421-423

  Gao, Shih Yu ^a   Lin, Yen Lin ^a   Rao, Polisetti Dharma ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

2 Methoxyphenols; Diels Alder reactions; Electron rich dienophiles; Masked o benzoquinones

Indexed keywords

BENZENE DERIVATIVE; BENZOQUINONE DERIVATIVE; BENZYL DERIVATIVE; FURAN DERIVATIVE; KETONE DERIVATIVE; STYRENE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0034009417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

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33. General procedures for the Diels-Alder reactions. Procedure A: To a solution of a 2-methoxyphenol 2 (1 mmol) in anhydrous MeOH (10 ml) was added DAIB (1.1 mmol) as a solid at 0°C. After 10 min of stirring, a dienophile (refer to Table) was added and the stirring was continued at room temperature for an appropriate period of time (see Table for specific cases) until the reaction was complete as indicated by TLC (disappearance of deep yellow color). Then all the volatiles were stripped-off under reduced pressure and the residue was purified by column chromatography on silica gel using 25% ethyl acetate in hexanes as eluent to obtain the desired adducts. Procedure B: To a mixture of 2-methoxyphenol 2 (1 mmol) and a dienophile (refer to Table) in MeOH (4 ml) was added DAIB (2 mmol) in MeOH (6 ml) during a period of time with the aid of a syringe pump at an appropriate temperature (see Table for specific cases). Then the reaction mixture was stirred further for 1 hr at that temperature and stripped off all the volatiles under reduced pressure. The adducts were purified as described in procedure A. Procedure C: To a mixture of DAIB (2 mmol) and a dienophile (25 mmol) in MeOH (4 ml) was added 2-methoxyphenol 2 (1 mmol) in MeOH (6 ml) during 4 h with the aid of a syringe pump at 50°C. Then the reaction mixture was stirred further for 1 hr at that temperature and worked up as described in procedure A.
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