First Tandem Asymmetric Conjugate Addition of Alkenyl Nucleophiles and Silyl Trapping of the Intermediate Enolates

The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)‐catalyzed addit...

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Published inAdvanced synthesis & catalysis Vol. 355; no. 13; pp. 2651 - 2658
Main Authors Westmeier, Johannes, Pfaff, Christopher, Siewert, Jürgen, von Zezschwitz, Paultheo
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.09.2013
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Asymmetry
Chemistry
Chemistry, Applied
Chemistry, Organic
Chlorides
conjugate addition
Conjugates
enones
Ethers
Nucleophiles
Physical Sciences
rhodium
Science & Technology
Synthesis
Trapping
Zirconium
ENANTIOSELECTIVE SYNTHESIS
ALDOL REACTIONS
asymmetric catalysis
conjugate addition
enones
STREPTOMYCES SP
RHODIUM-CATALYZED 1,4-ADDITION
KINETIC RESOLUTION
DIENE LIGANDS
SPIRODIONIC ACID
zirconium
PHOSPHINE-PHOSPHITE LIGANDS
GRIGNARD-REAGENTS
rhodium
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Abstract The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)‐catalyzed addition of readily available alkenylzirconocenes. As prerequisite for silyl trapping, the initially formed enolates have to be transmetalated from zirconium to lithium by treatment with methyllithium prior to addition of the silyl chloride. Starting from 5‐ to 7‐membered cycloalkenones, the respective silyl enol ethers were obtained in excellent yields and ≥93% ee; an acyclic substrate furnished a moderate enantioselectivity. Besides trimethylsilyl chloride, the silylation was also performed with tert‐butyldimethylsilyl chloride, and the synthetic scope was evaluated by employing five different alkenyl groups. Moreover, the mechanism of this sequence was elucidated by 1H NMR studies, and the efficiency of catalyst control was exemplified by synthesis of a cis‐3,5‐disubstituted cyclohexanone which, due to strong substrate control, cannot be obtained by copper‐catalyzed conjugate addition.
AbstractList The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)‐catalyzed addition of readily available alkenylzirconocenes. As prerequisite for silyl trapping, the initially formed enolates have to be transmetalated from zirconium to lithium by treatment with methyllithium prior to addition of the silyl chloride. Starting from 5‐ to 7‐membered cycloalkenones, the respective silyl enol ethers were obtained in excellent yields and ≥93% ee; an acyclic substrate furnished a moderate enantioselectivity. Besides trimethylsilyl chloride, the silylation was also performed with tert‐butyldimethylsilyl chloride, and the synthetic scope was evaluated by employing five different alkenyl groups. Moreover, the mechanism of this sequence was elucidated by 1H NMR studies, and the efficiency of catalyst control was exemplified by synthesis of a cis‐3,5‐disubstituted cyclohexanone which, due to strong substrate control, cannot be obtained by copper‐catalyzed conjugate addition.
Abstract The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)‐catalyzed addition of readily available alkenylzirconocenes. As prerequisite for silyl trapping, the initially formed enolates have to be transmetalated from zirconium to lithium by treatment with methyllithium prior to addition of the silyl chloride. Starting from 5‐ to 7‐membered cycloalkenones, the respective silyl enol ethers were obtained in excellent yields and ≥93% ee ; an acyclic substrate furnished a moderate enantioselectivity. Besides trimethylsilyl chloride, the silylation was also performed with tert ‐butyldimethylsilyl chloride, and the synthetic scope was evaluated by employing five different alkenyl groups. Moreover, the mechanism of this sequence was elucidated by 1 H NMR studies, and the efficiency of catalyst control was exemplified by synthesis of a cis ‐3,5‐disubstituted cyclohexanone which, due to strong substrate control, cannot be obtained by copper‐catalyzed conjugate addition. magnified image
The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)-catalyzed addition of readily available alkenylzirconocenes. As prerequisite for silyl trapping, the initially formed enolates have to be transmetalated from zirconium to lithium by treatment with methyllithium prior to addition of the silyl chloride. Starting from 5- to 7-membered cycloalkenones, the respective silyl enol ethers were obtained in excellent yields and 93% ee; an acyclic substrate furnished a moderate enantioselectivity. Besides trimethylsilyl chloride, the silylation was also performed with tert-butyldimethylsilyl chloride, and the synthetic scope was evaluated by employing five different alkenyl groups. Moreover, the mechanism of this sequence was elucidated by (HNMR)-H-1 studies, and the efficiency of catalyst control was exemplified by synthesis of a cis-3,5-disubstituted cyclohexanone which, due to strong substrate control, cannot be obtained by copper-catalyzed conjugate addition.
The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl enol ethers. Herein, the first method for the respective addition of alkenyl groups is reported, which is based on a rhodium(I)-catalyzed addition of readily available alkenylzirconocenes. As prerequisite for silyl trapping, the initially formed enolates have to be transmetalated from zirconium to lithium by treatment with methyllithium prior to addition of the silyl chloride. Starting from 5- to 7-membered cycloalkenones, the respective silyl enol ethers were obtained in excellent yields and greater than or equal to 93% ee; an acyclic substrate furnished a moderate enantioselectivity. Besides trimethylsilyl chloride, the silylation was also performed with tert-butyldimethylsilyl chloride, and the synthetic scope was evaluated by employing five different alkenyl groups. Moreover, the mechanism of this sequence was elucidated by super(1)H NMR studies, and the efficiency of catalyst control was exemplified by synthesis of a cis-3,5-disubsti-tuted cyclohexanone which, due to strong substrate control, cannot be obtained by copper-catalyzed conjugate addition.
Author Westmeier, Johannes
Pfaff, Christopher
Siewert, Jürgen
von Zezschwitz, Paultheo
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Issue 13
Keywords ENANTIOSELECTIVE SYNTHESIS
ALDOL REACTIONS
asymmetric catalysis
conjugate addition
enones
STREPTOMYCES SP
RHODIUM-CATALYZED 1,4-ADDITION
KINETIC RESOLUTION
DIENE LIGANDS
SPIRODIONIC ACID
zirconium
PHOSPHINE-PHOSPHITE LIGANDS
GRIGNARD-REAGENTS
rhodium
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WILEY‐VCH Verlag
Wiley
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Snippet The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable silyl...
Abstract The tandem asymmetric conjugate addition of alkyl or aryl groups to enones and subsequent silyl trapping has already been achieved and yields valuable...
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SubjectTerms asymmetric catalysis
Asymmetry
Chemistry
Chemistry, Applied
Chemistry, Organic
Chlorides
conjugate addition
Conjugates
enones
Ethers
Nucleophiles
Physical Sciences
rhodium
Science & Technology
Synthesis
Trapping
Zirconium
Title First Tandem Asymmetric Conjugate Addition of Alkenyl Nucleophiles and Silyl Trapping of the Intermediate Enolates
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