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Volumn 11, Issue 10, 2005, Pages 2954-2965

Stereoselective synthesis of highly enantioenriched (E)-allylsilanes by palladium-catalyzed intramolecular bis-silylation: 1,3-chirality transfer and enantioenrichment via dimer formation

Author keywords

Asymmetric synthesis; Dimerization; Palladium catalyst; Silicon; Silylation

Indexed keywords

ALCOHOLS; CATALYSIS; CATALYSTS; DIMERIZATION; DIMERS; PALLADIUM; SILICON; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 18744397258     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401031     Document Type: Article
Times cited : (39)

References (76)
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    • For the closely related cycloaddition with allenylsilanes, see
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    • 0001533637 scopus 로고
    • Asymmetric cross-coupling of α-(silyl)alkyl Grignard reagents to alkenyl bromides in the presence of chiral ferrocenylphosphine-palladium complexes: a) T. Hayashi, M. Konishi, H. Ito, M. Kumada, J. Am. Chem. Soc. 1982, 104, 4962;
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4962
    • Hayashi, T.1    Konishi, M.2    Ito, H.3    Kumada, M.4
  • 24
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    • Regioselective nucleophilic substitution of enantioenriched allylic esters and carbamates with (organosilyl)cuprates: a) I. Fleming, A. P. Thomas, J. Chem. Soc. Chem. Commun. 1986, 1456;
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    • Fleming, I.1    Thomas, A.P.2
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    • note
    • See ref. [18b] for some attempts at IBS of allylic alcohols with terminal C=C bonds.
  • 53
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    • The requisite chlorodisilanes were readily prepared by the reaction of (diethylamino)diphenylsilyllithium with the corresponding tri(organo) chlorosilanes followed by treatment with acetyl chloride, a) K. Tamao, A. Kawachi, Y. Ito, J. Am. Chem. Soc. 1992, 114, 3989-3990;
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3989-3990
    • Tamao, K.1    Kawachi, A.2    Ito, Y.3
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    • 18744363579 scopus 로고    scopus 로고
    • note
    • 2 axis passing through the center of the eight-membered ring, while achiral-4d has an inversion center at the center of the ring.
  • 57
    • 18744379399 scopus 로고    scopus 로고
    • note
    • The ee determination was carried out according to the procedure that includes reduction of the C=C bond with diimide followed by oxidation of the Si-C bond as described below.
  • 62
    • 18744402123 scopus 로고    scopus 로고
    • note
    • In reality, the dimerization took place with slight preference for the achiral dimer as shown in Scheme 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.