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Volumn 132, Issue 10, 2010, Pages 3612-3620

On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC BROMIDES; CROSS-COUPLINGS; ELECTROPHILES; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED CROSS-COUPLINGS; SILANOLATES; SITE-SELECTIVITY; STEREOSPECIFICITY; TRANSMETALATION;

EID: 77949388897     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910804u     Document Type: Article
Times cited : (58)

References (74)
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    • Recently developed, transition-metal-catalyzed additions of organic groups to aldehydes and imines are also not considered to be crosscoupling reactions. See: (a) Skukas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc Chem. Res. 2007, 40, 1394-1401.
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    • Chiral, olefinic ligands are widely employed in asymmetric, transitionmetal-catalyzed reactions. However, their use in asymmetric, palladium-catalyzed reactions remains elusive. See: Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482-4502.
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    • Trauner reported the preparation of a chiral diene-ligated palladium catalyst; however, the use of this catalyst in a palladium ene reaction provided only racemic products. See: Grundl, M. A.; Kennedy-Smith, J. J.; Trauner, D. Organometallics 2005, 24, 2831-2833.
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    • starcingmaterial) × 100%] provides a convenient method of describing the conservation of configurational purity for a reaction.
    • starcingmaterial) × 100%] provides a convenient method of describing the conservation of configurational purity for a reaction.
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    • N2′ reaction of Grignard reagents with allylic carbamates; see ref 23d. However, the stereochemical identity and purity of the α-substituted allylic silanol was too important to be assumed from analogous precedent.
    • N2′ reaction of Grignard reagents with allylic carbamates; see ref 23d. However, the stereochemical identity and purity of the α-substituted allylic silanol was too important to be assumed from analogous precedent.
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    • - was used for cross-coupling optimization and was synthesized by a similar route using racemic 13.
    • - was used for cross-coupling optimization and was synthesized by a similar route using racemic 13.
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    • The crotylation of bromobenzene with sodium 2-butenyldimethylsilanolate under these conditions provides high γ-selectivity (26:1) as determined by GC/MS analysis of the crude reaction mixture. See ref 15.
    • The crotylation of bromobenzene with sodium 2-butenyldimethylsilanolate under these conditions provides high γ-selectivity (26:1) as determined by GC/MS analysis of the crude reaction mixture. See ref 15.
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    • 0C, 69% yield (5.2:1 E-γ/α.).
    • 0C, 69% yield (5.2:1 E-γ/α.).
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    • By analogy, the absolute configurations of 23b, 20f, and 23h are assigned as S, R, and S, respectively.
    • By analogy, the absolute configurations of 23b, 20f, and 23h are assigned as S, R, and S, respectively.
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    • - has the secondary effect of removing the contribution of the minor enantiomer to the product mixture; see refs 23c, d.
    • - has the secondary effect of removing the contribution of the minor enantiomer to the product mixture; see refs 23c, d.
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    • In other closed, transition-state structures of palladium-catalyzed allylations, the vinylic methyl group positioned coplanar with the square plane of palladium ligands was suggested to be disfavored. See: Iwasaki, M.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4463-4469.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.