Synthesis of 3-alkylidenebicyclo[3.2.1]octan-8-one skeleton from the Baylis-Hillman acetates

Synlett

Volumn , Issue 6, 2003, Pages 821-824

  Kim, Jae Nyoung ^a   Kim, Jeong Mi ^a   Lee, Ka Young ^a  

^a Chonnam National University   (South Korea)

Author keywords

3 alkylidenebicyclo 3.2.1 octan 8 one; Baylis Hillman acetate; Kinetically controlled conditions

Indexed keywords

ACETIC ACID; ALCOHOL; BICYCLO[3.2.1]OCTANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; ETHYL 2 OXOCYCLOPENTANECARBOXYLATE; PHENOL DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION KINETICS; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038294333     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38750     Document Type: Article

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17. +, 84).
18. 3 (1.1 equiv) at reflux temperature for 30 min gave the thermodynamic products 5a (36%) and 6a (20%).
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23. The stereochemistry of 4a was confirmed by NOE experiments (Figures 1). The stereochemistry between the methyl group at C-2 position and the proton at C-1 position migth be cis relationship