SCOPUS 정보 검색 플랫폼

Volumn 2, Issue 11, 1991, Pages 1097-1100

On the way to chiral copper(I) arenethiolate catalysts for the enantioselective conjugate addition of methyl lithium and methyl magnesium iodide to benzylideneacetone

(6) Lambert, Francois a Knotter, D Martin a Janssen, Maurits D a van Klaveren, Mayra a Boersma, Jaap a van Koten, Gerard a

a UTRECHT UNIVERSITY (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0025937497 PISSN: 09574166 EISSN: 1362511X Source Type: Journal
DOI: 10.1016/S0957-4166(00)82005-4 Document Type: Article

Times cited : (85)

References (20)

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- D.M. Knotter, D.M. Grove, W.J.J. Smeets, A.L. Spek, and G. van Koten, J. Am. Chem. Soc., accepted.

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- 3. However, for clarity it will be considered as a monomer in this report.

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- At these ratios (order of addition of the reagents) the enolate formation is competitive with the addition reactions of organocuprate reagents, in particular with the more acidic methylketones
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- Hallnemo¹ Ullenius²

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- Christenson¹ Ullenius²

17
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- In a recent study we found that subsequent condensation of benzylideneacetone with two equivalents of its lithium enolate, results in the formation of a tri-Michael product (15% yield, unique stereochemistry established by an X-ray crystallographic study) F. Lambert, A.L. Spek, J. Boersma, and G. van Koten, to be published.

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- 2O, toluene and hexane. Hydrolyses of this cuprate with water and measurement of the amount of methane evolved confirmed the proposed 1/1 molar ratio.

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- With smaller amounts of [CuSAr*] catalyst lower selectivities for 1,4- vs. 1,2-addition were found, above 9 mol % the e.e. values remain the same.

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- in press
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