Gold-catalyzed synthesis of bicyclo[4.3.0]nonadiene derivatives via tandem 6-endo-dig/Nazarov cyclization of 1,6-allenynes

Journal of Organic Chemistry

Volumn 72, Issue 18, 2007, Pages 6753-6757

  Lin, Guan You ^a   Yang, Chun Yao ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD CATALYZED SYNTHESIS; NONADIENE DERIVATIVES; SUBSTRATE BEARINGS;

CATALYSIS; CYCLIZATION; DERIVATIVES; GOLD; REACTION KINETICS; SYNTHESIS (CHEMICAL);

OLEFINS;

ALKYL GROUP; ALLENE DERIVATIVE; BICYCLO COMPOUND; BICYCLO[4.3.0]NONADIENE DERIVATIVE; GOLD DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; NAZAROV CYCLIZATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 34548757875     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0707939     Document Type: Article

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52. 15 one alternative mechanism involves initial Nazarov cyclization, followed by 6-endo-dig cyclization of π-alkyne H as depicted below; the initial intermediate is Au(I)-π-allene intermediate F′, which activates indene formation to give species G. After protodeauration, a subsequent 6-endo-dig cyclization of alkyne intermediate H provides the desired bicyclo[4.3.0]nonadiene 5a. This pathway, however, is opposed by formation of cyclopentol 6, which indicates initial formation of a cyclopentene ring rather than the indene ring. (Chemical Equation Presented)