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Volumn 45, Issue 4, 1997, Pages 651-658

Dirhodium(II)-catalyzed intramolecular carbon-hydrogen insertion reaction of α-diazoketones: Synthesis of 7-silyloxyoctahydrobenzo[b]furan- 2-ones

Author keywords

carbon hydrogen insertion reaction; dirhodium(II) tetraacetate; octahydrobenzo b furan 2 one; regioselectivity; lactone

Indexed keywords

7 SILYLOXYOCTAHYDROBENZO[B]FURAN 2 ONE; CYCLOHEXANE DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; LACTONE DERIVATIVE; RHODIUM TETRAACETATE; UNCLASSIFIED DRUG;

EID: 0030906379     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.651     Document Type: Article
Times cited : (9)

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