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Volumn 50, Issue 32, 2011, Pages 7308-7311

Macrocyclization of oxetane building blocks with diazocarbonyl derivatives under rhodium(II) catalysis

Author keywords

diazo compounds; macrocycles; oxetanes; rhodium; ylides

Indexed keywords

BUILDING BLOCKES; DIAZO COMPOUNDS; HIGH CONCENTRATION; MACRO-CYCLIZATION; MACROCYCLES; OXETANES; YLIDES;

EID: 79960903370     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102152     Document Type: Article
Times cited : (59)

References (61)
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    • Of importance, polymerization reactions do not occur upon mixing oxetanes and rhodium(II) complexes.
    • Of importance, polymerization reactions do not occur upon mixing oxetanes and rhodium(II) complexes.
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    • The 1 M concentration was maintained throughout the study. It corresponds to a molar ratio of ca. 15:1 between oxetane molecules and diazocarbonyls 2.
    • The 1 M concentration was maintained throughout the study. It corresponds to a molar ratio of ca. 15:1 between oxetane molecules and diazocarbonyls 2.
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    • Care should be taken to use neutral alumina instead of silica gel for the purification as unsaturated derivatives of type 3 are sensitive to acids.
    • Care should be taken to use neutral alumina instead of silica gel for the purification as unsaturated derivatives of type 3 are sensitive to acids.
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    • 6] and diimine ligands were used. For use of these later complexes as diazo decomposition catalysts, see.
    • 6] and diimine ligands were used. For use of these later complexes as diazo decomposition catalysts, see, M. Austeri, D. Rix, W. Zeghida, J. Lacour, Org. Lett. 2011, 13, 1394-1397.
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    • Austeri, M.1    Rix, D.2    Zeghida, W.3    Lacour, J.4
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    • This result contrasts with that obtained in the reaction of 2 e with 1,4-dioxane (Ref. [9d]). In that case, an important amount of cyclopropane adduct was observed along with the 18-membered macrocycle.
    • This result contrasts with that obtained in the reaction of 2 e with 1,4-dioxane (Ref. [9d]). In that case, an important amount of cyclopropane adduct was observed along with the 18-membered macrocycle.
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    • Ref. [1a]
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    • Interestingly, literature precedents on the photochemical decomposition of diazo derivatives in oxetane medium also indicate the preferred formation of 15-membered macrocycles albeit in lower yields. See Ref. [7].
    • Interestingly, literature precedents on the photochemical decomposition of diazo derivatives in oxetane medium also indicate the preferred formation of 15-membered macrocycles albeit in lower yields. See Ref. [7].
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    • H,H coupling constant occurring between the protons α to the ester and methyl groups is consistent with a cis and not a trans configuration of product 10.
    • H,H coupling constant occurring between the protons α to the ester and methyl groups is consistent with a cis and not a trans configuration of product 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.