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Volumn 661, Issue 1-2, 2002, Pages 31-47

The lactone concept - A novel approach to the metal-assisted atroposelective construction of axially chiral biaryl systems

Author keywords

Atropisomers; Axial chirality; Biaryls; Dynamic kinetic resolution; Ring opening; Stereoselective synthesis

Indexed keywords

AROMATIC COMPOUND; BRIDGED COMPOUND; CHROMIUM DERIVATIVE; COORDINATION COMPOUND; ESTER DERIVATIVE; LACTONE; LEWIS ACID; METAL DERIVATIVE; RUTHENIUM COMPLEX;

EID: 0036829527     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(02)01804-1     Document Type: Article
Times cited : (87)

References (131)
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    • Recently, two examples for the catalytic asymmetric synthesis of axially chiral biaryls using chiral Pd-catalysts were published. However, these methods are not yet applicable to the synthesis of a broader range of biaryls
    • Recently, two examples for the catalytic asymmetric synthesis of axially chiral biaryls using chiral Pd-catalysts were published. However, these methods are not yet applicable to the synthesis of a broader range of biaryls: J. Yin, S.L. Buchwald, J. Am. Chem. Soc. 122 (2000) 12051;
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    • For a very special exception occurred in the syntheses of vancomycin (2, see Fig. 1), in which the initially 'wrong' configuration at the biaryl axis was corrected by thermodynamically controlled atropo-diastereomeric equilibration as achieved by heating, due to the low steric hindrance in the proximity of the axis; see:
    • For a very special exception occurred in the syntheses of vancomycin (2, see Fig. 1), in which the initially 'wrong' configuration at the biaryl axis was corrected by thermodynamically controlled atropo-diastereomeric equilibration as achieved by heating, due to the low steric hindrance in the proximity of the axis; see: D.A. Evans, M.R. Wood, B.W. Trotter, T.I. Richardson, J.C. Barrow, J.L. Katz, Angew. Chem. 110 (1999) 2864;
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    • The absolute configuration of (P,R)-39c was determined by oxidative degradation
    • The absolute configuration of (P,R)-39c was determined by oxidative degradation: G. Bringmann, M. Münchbach, M. Michel, Tetrahedron Asymm. 11 (2000) 3167.
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    • For accompanying quantumchemical calculations see ref. [47]
    • For accompanying quantumchemical calculations see ref. [47].
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    • A related case in which-now due to the presence of stereogenic centers-an atropo-diastereomeric equilibrium is fully on the side of one particular atropisomer, occurred in the syntheses of the naphthylisoquinoline alkaloids ancistrocladine and dioncophylline C, see Refs. [67,68,11]
    • A related case in which-now due to the presence of stereogenic centers-an atropo-diastereomeric equilibrium is fully on the side of one particular atropisomer, occurred in the syntheses of the naphthylisoquinoline alkaloids ancistrocladine and dioncophylline C, see Refs. [67,68,11].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.