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Volumn 70, Issue 24, 2005, Pages 9667-9676

Catalytic, enantioselective α-additions of isocyanides: Lewis base catalyzed Passerini-type reactions

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; ESTERS; METHANOL; SILICON;

EID: 28044462675     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050549m     Document Type: Article
Times cited : (117)

References (76)
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    • Lowering the concentration of the isocyanide may also disfavor the background reaction if the order in isocyanide is higher in this process than in the catalyzed addition. By analogy to other reactions, we expect that the isocyanide is first order in the catalyzed process: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022.
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    • Discussion and Supporting Information
    • In the presence of Hünig's base, reaction of 2d with benzaldehyde afforded 8 in 43% yield along with a double addition product 13 in 10% yield. Under these conditions, 2e afforded 9 in 64% yield along with two byproducts, benzoin (14a) in 9% yield and tosylmethylformamide (14b) in 7% yield; see the Discussion and Supporting Information.
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    • note
    • A number of experiments were performed with (S)-1-phenylethyl isocyanide to determine the influence of a chiral isocyanide alone and in double diastereoselection with catalyst (R,R)-1b. In the addition to benzaldehyde, high yields were obtained, but in no case was the influence of the stereogenic center on the isocyanide manifested.
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    • For the IUPAC definitions of catalyst and pseudocatalyst see http://www.chem.qmul.ac.uk/iupac/gtpoc/.
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    • note
    • The calculations on a complex of benzaldehyde and the dimeric phosphoramide (R,R)-1b bound trichlorosilyl cation were performed using the PC version of GAMESS(US) QC Package employing the PM3 basis set.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.