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Volumn 50, Issue 40, 2009, Pages 5652-5655

Highly enantioselective Diels-Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG; UREA; YTTERBIUM; YTTERBIUM TRIFLATE;

EID: 68749116415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.110     Document Type: Article
Times cited : (26)

References (63)
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    • See also Ref. 10. By the addition of tertiary amine, DA adducts can be isolated as 4, and the excess diene remained unchanged during the reaction as well. Without amines, DA adducts were directly converted to 5
    • Nishida A., Yamanaka M., and Nakagawa M. Tetrahedron Lett. 40 (1999) 1555 See also Ref. 10. By the addition of tertiary amine, DA adducts can be isolated as 4, and the excess diene remained unchanged during the reaction as well. Without amines, DA adducts were directly converted to 5
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    • note
    • Recently, both isomers of optically active 6,6′-dimethyl-2,2′-biphenyldiamine (6) have become commercially available from Aldrich. The absolute configuration of 9 synthesized from (±)-6 was determined by comparison to the spectral data of 9 synthesized from purchased optically pure 6.
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    • note
    • For these optimized conditions with (S)-10a (10 mol %): 7% yield; -76% ee. (S)-10a was still mismatched ligand.
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    • note
    • Without this operation, we did not obtain reproducible results. A precise mechanistic investigation is now underway.
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    • note
    • For the reaction of 2a and 3a, (R)-10c has similar reactivity and selectivity to (R)-10a. But, for 2a and 3h, (R)-10c gave only 12% yield and 84% ee (0.6 M, 0 °C, 3 h).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.