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Volumn 54, Issue 51, 2015, Pages 15497-15500

Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts

Author keywords

aminothiourea; cascade reactions; natural products; organocatalysis; spiroketals

Indexed keywords

ENANTIOSELECTIVITY; HYDROGEN BONDS; SYNTHESIS (CHEMICAL);

EID: 84955185859     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201508405     Document Type: Article
Times cited : (54)

References (65)
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    • An analogous cascade reaction to afford spiroketals was previously reported, although this is not a catalytic reaction, and the stereoselectivity is only modest.
    • An analogous cascade reaction to afford spiroketals was previously reported, although this is not a catalytic reaction, and the stereoselectivity is only modest:, M. Tiecco, L. Testaferri, L. Bagnoli, C. Scarponi, A. Temperini, F. Marini, C. Santi, Tetrahedron: Asymmetry 2006, 17, 2768.
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    • Tiecco, M.1    Testaferri, L.2    Bagnoli, L.3    Scarponi, C.4    Temperini, A.5    Marini, F.6    Santi, C.7
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    • Analogous biosynthetic reactions
    • Analogous biosynthetic reactions:
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    • For selected examples of synthesis of 2-alkylspiroketals, see Refs.[1j, 3, 8] and
    • For selected examples of synthesis of 2-alkylspiroketals, see Refs.[1j, 3, 8] and:
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    • Starting materials 1 were prepared through the synthetic routes described in the Supporting Information. Although the shorter route was employed only for the synthesis of 1 f and 1 g, it would also be applicable to the synthesis of other substrates.
    • Starting materials 1 were prepared through the synthetic routes described in the Supporting Information. Although the shorter route was employed only for the synthesis of 1 f and 1 g, it would also be applicable to the synthesis of other substrates.
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    • A substrate bearing a racemic secondary alcohol was also investigated to afford a disubstituted spiroketal; two diastereomers were preferentially obtained with high enantioselectivities (82 %, d.r.=11:9.2:2.2:1, 92 % ee/73 % ee/97 % ee/33 % ee), while the recovered starting material was nearly racemic (17 %, 4 % ee; see the Supporting Information).
    • A substrate bearing a racemic secondary alcohol was also investigated to afford a disubstituted spiroketal; two diastereomers were preferentially obtained with high enantioselectivities (82 %, d.r.=11:9.2:2.2:1, 92 % ee/73 % ee/97 % ee/33 % ee), while the recovered starting material was nearly racemic (17 %, 4 % ee; see the Supporting Information).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.