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Volumn 45, Issue 14, 2006, Pages 2254-2257

High substrate/catalyst organocatalysis by a chiral Brønsted acid for an enantioselective aza-ene-type reaction

Author keywords

Asymmetric synthesis; Br nsted acids; Ene reaction; Organocatalysis; Phosphoric acid

Indexed keywords

ACIDS; AROMATIC COMPOUNDS; CATALYST ACTIVITY; DERIVATIVES; PHOSPHORIC ACID; SUBSTRATES;

EID: 33746292951     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503477     Document Type: Article
Times cited : (248)

References (58)
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    • For some excellent studies describing high S/C (greater than 200:1) organocatalysis, see: a) J. T. Su, P. Vachal, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 197-200;
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    • note
    • The absolute configuration of 5 (Ar = Ph) was determined to be R (see the Supporting Information).
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    • note
    • We employed the acetone-derived enecarbamate 8 instead of the acetophenone-derived enecarbamate 3d to expand the substrate scope. The reaction of 8 with imine 2 (Ar = Ph) worked well under the high S/C conditions (0.1 mol% of 1), and subsequent hydrolysis gave the corresponding product 9 in good yield (80%). Unfortunately, however, the enantiomeric excess was moderate (44% ee); further screening of the catalyst, reactants, and reaction conditions is required to improve the enantiomeric excess (see Supporting Information).
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    • see also Ref. [7a] and references therein
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    • note
    • A single geometric isomer of 4 was obtained, but the configuration has not yet been determined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.