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Volumn 50, Issue 32, 2011, Pages 7354-7358

Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks

Author keywords

azides; Claisen rearrangement; gold; homogeneous catalysis; nitrogen heterocycles

Indexed keywords

BIOACTIVITY; CATALYSIS; GOLD;

EID: 79960909487     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102707     Document Type: Article
Times cited : (242)

References (68)
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    • No example of such a Claisen rearrangement has been reported in the literature.
    • No example of such a Claisen rearrangement has been reported in the literature.
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    • Compound 16 e was isolated with a small amount of the ortho-substituted phenol regioisomer (9:1 ratio; see the Supporting Information for more details). For other selected examples of gold-catalyzed Friedel-Crafts reactions, see
    • Compound 16 e was isolated with a small amount of the ortho-substituted phenol regioisomer (9:1 ratio; see the Supporting Information for more details). For other selected examples of gold-catalyzed Friedel-Crafts reactions, see
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    • Intermediate 19 could also be produced from iminium 18.
    • Intermediate 19 could also be produced from iminium 18.
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    • No cyclopropanation products were formed when 8 was treated with 8 mol % of gold complex 13 and 10 equiv of styrene.
    • No cyclopropanation products were formed when 8 was treated with 8 mol % of gold complex 13 and 10 equiv of styrene.
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    • The carbene reactivity is not supported by the selectivity observed in the formation of the 3-arylated indoles 16 e - g (Table 3, entries 5 and 6).
    • The carbene reactivity is not supported by the selectivity observed in the formation of the 3-arylated indoles 16 e-g (Table 3, entries 5 and 6).
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    • The moderate selectivity observed in the Claisen products is possibly due to steric effects that do not favor a chairlike over a boatlike transition-state intermediate.
    • The moderate selectivity observed in the Claisen products is possibly due to steric effects that do not favor a chairlike over a boatlike transition-state intermediate.
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    • 3 as solvent), the postulated 3-allyloxyindole intermediate 10 could not be observed. This result tends to support a reaction pathway involving a rapid Claisen rearrangement via gold complex 21 or a reaction pathway involving the iminium species 23.
    • 3 as solvent), the postulated 3-allyloxyindole intermediate 10 could not be observed. This result tends to support a reaction pathway involving a rapid Claisen rearrangement via gold complex 21 or a reaction pathway involving the iminium species 23.
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    • The use of the sterically congested nucleophile (-)-myrtenol did not result in the Claisen rearrangement, and only compound 29 could be obtained.
    • The use of the sterically congested nucleophile (-)-myrtenol did not result in the Claisen rearrangement, and only compound 29 could be obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.