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Volumn 54, Issue 6, 2015, Pages 1910-1913

Enantioselective formation of all-carbon quaternary stereocenters from indoles and tertiary alcohols bearing a directing group

Author keywords

Asymmetric catalysis; Enantioselectivity; Heterocycles; Organocatalysis; Synthetic methods

Indexed keywords

CARBON; CATALYSIS; REACTION KINETICS;

EID: 85027918784     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405252     Document Type: Article
Times cited : (254)

References (102)
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    • Current examples are limited to indol-3-yl carbocations, which were viewed as extended iminiums
    • Current examples are limited to indol-3-yl carbocations, which were viewed as extended iminiums:
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    • Our effort in chiral acid catalysis
    • Our effort in chiral acid catalysis:
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    • Chiral anion induction for tertiary carbocations remains challenging. For some reviews
    • Chiral anion induction for tertiary carbocations remains challenging. For some reviews:
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    • For some examples of conjugate addition to b,b-disubstituted enones to generate all-carbon quaternary stereocenters, see
    • For some examples of conjugate addition to b,b-disubstituted enones to generate all-carbon quaternary stereocenters, see:
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    • for some examples with b,bdisubstituted nitroalkenes, see
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    • o-Quinone methides (o-QMs) are important species in organic synthesis. However, their catalytic asymmetric reactions are scarce. To our knowledge, catalytic asymmetric reactions of b,bdisubstituted o-QMs are unknown. For some reviews
    • o-Quinone methides (o-QMs) are important species in organic synthesis. However, their catalytic asymmetric reactions are scarce. To our knowledge, catalytic asymmetric reactions of b,bdisubstituted o-QMs are unknown. For some reviews:
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    • No kinetic resolution of the starting material 1a was observed, that is, at partial conversion the starting alcohol remained racemic
    • a) No kinetic resolution of the starting material 1a was observed, that is, at partial conversion the starting alcohol remained racemic.
  • 95
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    • With the enantioenriched 1a (97% ee) as the starting material, the product 3a was formed in comparable enantiomeric excess (90% ee). At partial conversion, the ee values of the starting 1a and the product 3a both remained essentially constant, thus suggesting an irreversible first step
    • )With the enantioenriched 1a (97% ee) as the starting material, the product 3a was formed in comparable enantiomeric excess (90% ee). At partial conversion, the ee values of the starting 1a and the product 3a both remained essentially constant, thus suggesting an irreversible first step.
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    • For examples, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.