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Volumn 14, Issue 6, 2012, Pages 1620-1623

Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALDEHYDE; CINCHONA ALKALOID; KETONE; THIOUREA;

EID: 84858670767     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3003755     Document Type: Article
Times cited : (72)

References (60)
  • 50
    • 38349013230 scopus 로고    scopus 로고
    • Reactions between γ-hydroxy-α,β-unsaturated ketones and boronic acids via boronic acid hemiester intermediates have been previously reported; see: Li, D. R.; Murugan, A.; Falck, J. R. J. Am. Chem. Soc. 2008, 130, 46
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 46
    • Li, D.R.1    Murugan, A.2    Falck, J.R.3
  • 60
    • 79957757640 scopus 로고    scopus 로고
    • Aryl and alkenyl aldehydes proved to be much less reactive: reactions using benzaldehyde or cinnamaldehyde with 1a gave the corresponding products in less than 10% yields, while electron-poor 4-(trifluoromethyl)benzaldehyde gave the acetal product in 70% yield with moderate stereoselectivities (dr = 0.9:1, 79% ee and 82% ee, respectively). Similar observations were also recently reported; see ref 5b. For quantification of the electrophilic reactivity of aldehydes, see: Appel, R.; Mayr, H. J. Am. Chem. Soc. 2011, 133, 8240
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8240
    • Appel, R.1    Mayr, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.