Study on the base-catalyzed reverse vinylogous aldol reaction of (4aβ,5β)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen- 2(3H)-one under Robinson annulation conditions

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 416-419

  Payette, Joshua N ^a   Honda, Tadashi ^a   Yoshizawa, Hidenori ^a   Favaloro Jr , Frank G ^a   Gribble, Gordon W ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; MIXTURES; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALDOL REACTIONS; REGIOSELECTIVITY; ROBINSON ANNULATION;

NAPHTHALENE;

4 (2,6 DIMETHYL 3 OXOCYCLOHEX 1 ENYL)BUTANAL; 4 (2,6 DIMETHYL 5 OXOCYCLOHEX 1 ENYL)BUTANAL; 4,4A,5,6,7,8 HEXAHYDRO 5 HYDROXY 1,4A DIMETHYLNAPHTHALEN 2(3H) ONE; BUTYRALDEHYDE; CYCLOHEXENE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; REACTION ANALYSIS; ROBINSON ANNULATION; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANIC CHEMICALS; VINYL COMPOUNDS;

EID: 31144434387     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520036     Document Type: Article

References (13)

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11. 12 This result shows that enolate III is produced kinetically from 21 and supports our belief that aldehyde 11 gives a complex product mixture via kinetic enolate II (Scheme 5).
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13. Extensive drying did not remove the water present in the sample.