Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones.

Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Research Abstract Details 

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Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Abstract Text:

Khalid Selim,Takahiro Soeta,Ken-ichi Yamada,Kiyoshi Tomioka,

The asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones under the catalysis of chiral amidophosphane-copper(I) complexes gave a mixture of nearly equal amounts of the corresponding trans- and cis-disubstituted cyclohexanones with extremely high catalyst-controlled enantioselectivity. Epimerization with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) led to the conversion of these mixtures into the thermodynamically more stable trans-2,5-disubstituted cyclohexanone as the major product with up to 96% ee in up to 96% yield. The regio- and stereoselective alkylation of the disubstituted cyclohexanone products via the thermodynamically favored enolate gave 2,2,5-trisubstituted cyclohexanones with a quaternary asymmetric carbon atom in good yield.

Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Publishing Authors By Initials

K Selim,T Soeta,K Yamada,K Tomioka,

For similar inorganic chemicals: zinc compounds research abstracts see: inorganic chemicals: zinc compounds research

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Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry, an Asian journal

VOLUME: 3

Page Numbers: 342-50

Journal Abbreviation:

ISSN: 1861-471X

DAY: 1

MONTH: Feb

YEAR: 2008

Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Information

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LANGUAGE: eng

NlmUniqueID: 101294643

Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Keywords Mesh Terms:

KEYWORDS: Zinc Compounds

MESH TERMS: chemistry

Chemical & Substance for Abstract: Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones. Information

Substance Name: phosphine

Registry Number: 7803-51-2

Grant and Affiliation Information for Amidophosphane-copper(I)-catalyzed asymmetric conjugate addition of dialkylzinc reagents to racemic 6-substituted cyclohexenones to form 2,5-di- and 2,2,5-trisubstituted cyclohexanones.

AFFILIATION: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.

Country: Germany

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MEDLINETA: Chem Asian J

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