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Volumn 54, Issue 5, 2015, Pages 1638-1641

Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes

Author keywords

Asymmetric synthesis; Copper; Hydroaminationsilicon

Indexed keywords

AMINO ACIDS; CATALYSIS; COPPER; REGIOSELECTIVITY; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 84921738702     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410326     Document Type: Article
Times cited : (120)

References (60)
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    • note
    • For vinylsilanes, the partial positive charge is more pronounced at the β-position (to the silicon) due to the β-silicon effect (see Refs. [12] and [13]). The partial negative charge that develops at the α-position is stabilized by the silyl group (see Refs. [14] and [15]). Furthermore, intermediate II (Scheme 3) is thermodynamically stabilized by hyperconjugation of the σ-orbital of the Cu-alkyl bond with a σ∗-orbital on the silicon-carbon bond (see Ref. [16]).
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    • note
    • The hydroamination reaction is slow for vinylsilanes with large silyl groups such as TIPS and TBDPS. After 36 h, no conversion was observed for (Z)-triisopropyl(5-phenylpent-1-en-1-yl)silane and only 16% conversion was observed for (Z)-tert-butyldiphenyl(5-phenylpent-1-en-1-yl)silane.
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    • (2014) Angew. Chem. , vol.126 , pp. 5054-5058


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.