C2-symmetric Cu(II) complexes as chiral Lewis acids. Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates [21]

Journal of the American Chemical Society

Volumn 121, Issue 9, 1999, Pages 1994-1995

  Evans, David A ^a   Rovis, Tomislav ^a   Kozlowski, Marisa C ^a   Tedrow, Jason S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; COPPER COMPLEX; MALONIC ACID DERIVATIVE; PROPANOL;

CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DECARBOXYLATION; LETTER; X RAY DIFFRACTION;

EID: 0033541094     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983864h     Document Type: Letter

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34. The use of the cosolvent is preferred for reasons of operational simplicity. The catalyst cannot be formed in toluene, and although the dichloromethane can be removed once the catalyst is formed, we have found the mixed solvent system to be superior in certain cases likely owing to solubility issues. Full details of this work will be published in due course.
35. Ligand recovery was 63%: see Supporting Information for details.
36. 3, Z = 3, R1 = 0.0397, wR2 = 0.0980, data/parameters = 7940/469, GOF = 1.019.
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39. In a related case the impact of nonbonding interactions imposed by carbonyl substituents in diastereoselective carbonyl addition has previously been noted: (a) Heathcock, C. H.; Flippin, L. A. J. Am. Chem. Soc. 1983, 105, 1667-1668. (b) Heathcock, C. H. Aldrichimica Acta 1990, 23, 99-111.
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