Highly enantioselective synthesis of 2,6-disubstituted and 2,2,6-trisubstituted dihydropyrones: A one-step synthesis of (R)-(+)-hepialone and its analogues

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8533-8537

  Yang, Weiqing ^a   Shang, Deju ^a   Liu, Yanling ^a   Du, Ying ^a   Feng, Xiaoming ^a,b  

^a China   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; SYNTHESIS (CHEMICAL);

CATALYTIC REACTION; ENANTIOSELECTIVE SYNTHESIS; HETEROAROMATIC ALDEHYDES;

AROMATIC COMPOUNDS;

4 METHOXY 2 TRIMETHYLSILOXY PENTA 1,3 DIENE; ALDEHYDE DERIVATIVE; ALUMINUM DERIVATIVE; DIHYDROPYRONE DERIVATIVE; HEPIALONE DERIVATIVE; PYRONE DERIVATIVE; PYRUVIC ACID DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; METHODOLOGY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 26844452226     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051458s     Document Type: Article

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60. 3 in petroleum ether.
61. 13C NMR and HRMS data; for details see Supporting Information.
62. The ee values was determined by HPLC using a chiralcel OJ column, and the racemate of 4o was acquired by the reaction of 2o with diene 1 catalized by (±)-BINOL; for details see Supporting Information.