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Volumn 133, Issue 6, 2011, Pages 1726-1729

Enantioselective [3 + 2] cycloaddition of allenes to acrylates catalyzed by dipeptide-derived phosphines: Facile creation of functionalized cyclopentenes containing quaternary stereogenic centers

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; CHIRAL PHOSPHINE; DIPEPTIDE; ENANTIOSELECTIVE; FUNCTIONALIZED CYCLOPENTENES; HIGH YIELD; REGIOSPECIFIC; STEREOGENIC CENTERS; STEREOSELECTIVE MANNER;

EID: 79951535933     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1106282     Document Type: Article
Times cited : (261)

References (77)
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    • l -Thr- d -Val-derived phosphine-thiourea catalyst (3d) was also prepared and examined in the cyclization, and the reaction was completed only after 24 h. The cycloaddition products were obtained in 85% yield, with an α to ? ratio of 90:10, and -28% ee for the α-isomer. See Supporting Information for details.
    • l -Thr- d -Val-derived phosphine-thiourea catalyst (3d) was also prepared and examined in the cyclization, and the reaction was completed only after 24 h. The cycloaddition products were obtained in 85% yield, with an α to ? ratio of 90:10, and -28% ee for the α-isomer. See Supporting Information for details.
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    • For a complete survey of influences of different solvents on the reaction, see the Supporting Information.
    • For a complete survey of influences of different solvents on the reaction, see the Supporting Information.
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    • The acrylate with a benzyl substitution has a rather flexible conformation compared to that of other α-aryl-substituted acrylates, which may introduce unfavorable steric interactions with the phosphonium enolate, resulting in a less-defined transition state and decreased enantioselectivity.
    • The acrylate with a benzyl substitution has a rather flexible conformation compared to that of other α-aryl-substituted acrylates, which may introduce unfavorable steric interactions with the phosphonium enolate, resulting in a less-defined transition state and decreased enantioselectivity.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.