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Volumn 63, Issue 15, 2007, Pages 3102-3107

Organocatalytic direct aldol and nitroaldol reactions between azetidine-2,3-diones and ketones or nitromethane

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; KETONE DERIVATIVE; METHYLEPHEDRINE; NITROMETHANE; PROLINE;

EID: 33847624210     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.024     Document Type: Article
Times cited : (12)

References (83)
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    • note
    • A typical reaction of azetidine-2,3-diones 1 was catalyzed (10 mol %) by N-benzylglycine and was conducted in acetone for a period of 2 days (conversion up to 5%).
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    • A typical reaction of azetidine-2,3-diones 1 was catalyzed (10 mol %) by the system pyrrolidine/acetic acid (1:1) and was conducted in acetone for a period of 24 h. In addition to the aldol product (yield up to 31%), some epimerization on the starting ketone was detected.
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    • Match implies that the catalyst reinforces the inherent diastereoselectivity of the substrate, and mismatch implies that the catalyst contradicts the inherent diastereoselectivity. With matched catalyst/substrate pairs, the selectivity is universally excellent. Furthermore, in every mismatched case, the catalyst is able to override and control the diastereoselectivity of the addition.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.