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Volumn 67, Issue 2, 2011, Pages 531-539

Synthesis of γ-amino alcohols from aldehydes, enamines, and trichlorosilane using Lewis base catalysts

Author keywords

Amino alcohol; Enamine; Lewis base catalysis; Tandem reaction; Trichlorosilane

Indexed keywords

ALDEHYDE; AMINOALCOHOL; ENAMINE; KETONE; LEWIS BASE; SILANE DERIVATIVE;

EID: 78650170316     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.075     Document Type: Article
Times cited : (14)

References (80)
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    • For NMR spectra of the reaction mixture and the assignment of the 1,2-anti iminium ion intermediate, see Supporting data
    • For NMR spectra of the reaction mixture and the assignment of the 1,2-anti iminium ion intermediate, see Supporting data.
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    • The diastereomeric ratios were determined by analogy
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    • note
    • The first C-C bond formation would be almost anti selective as depicted in Fig. 3 (see also Ref. 19) at low temperature. However, the enantioselectivity of this step would be low. If the enantio-determining step had been mainly this step, the enantiomeric excess of product 3a obtained under the conditions of entry 3 (Table 4) would have been at least 24% according to the results shown in entries 1 and 2. This assumption is evidently inconsistent with the actual result (9% ee). Therefore, the kinetic resolution of the anti iminium ion via the second intramolecular reduction would be mainly enantio-determining.


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