Synthesis of the Lithium Enolate of (S)-(+)-sec-Butyl Methyl Ketone and Formation of Chiral 1,3-Diketones by Acylation

Dieter Seebach; Volker Ehrig

doi:10.1002/anie.197201271

Synthesis of the Lithium Enolate of (S)-(+)-sec-Butyl Methyl Ketone and Formation of Chiral 1,3-Diketones by Acylation

Angewandte Chemie International Edition in English ◽

10.1002/anie.197201271 ◽

1972 ◽

Vol 11 (2) ◽

pp. 127-128 ◽

Cited By ~ 5

Author(s):

Dieter Seebach ◽

Volker Ehrig

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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Discussion Addendum for: [3 + 4] Annulation Using a [β-(Trimethylsilyl) acryloyl]silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S)-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo [5.4.0]undec-4-en-2-one

Organic Syntheses ◽

10.1002/0471264229.os089.26 ◽

2014 ◽

pp. 267-273

Author(s):

Kei Takeda ◽

Michiko Sasaki

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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Synthesis of Clavulones (Claviridenones) via [3+2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone

Synlett ◽

10.1055/s-1997-781 ◽

1997 ◽

Vol 1997 (3) ◽

pp. 255-256 ◽

Cited By ~ 18

Author(s):

Kei Takeda ◽

Akemi Nakajima ◽

Eiichi Yoshii

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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Efficient Trapping of Ketone Enolates With Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-Sulfinyl- and β-Chloro-Vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds

Australian Journal of Chemistry ◽

10.1071/ch9901375 ◽

1990 ◽

Vol 43 (8) ◽

pp. 1375 ◽

Cited By ~ 7

Author(s):

RJ Dancer ◽

RK Haynes ◽

WA Loughlin ◽

SC Vonwiller

Keyword(s):

Methyl Ketone ◽

Conjugate Addition ◽

Ring Closure ◽

High Yield ◽

Dicarbonyl Compounds ◽

Lithium Enolate ◽

Ketone Enolates ◽

Facile Preparation

Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2- enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol, and, in the presence of copper(I), a lactone derived from the hydrindanol. β-Sulfonylacrylate phenyl and t-butyl thioesters, β-chlorovinyl, β- sulfonyl- and β-sulfinyl-vinyl ketones react with the foregoing enolate, and with the enolate generated through conjugate addition of a methylcuprate to 2-methylcyclohexenone to give unsaturated 1,5-dicarbonyl compounds. The β-chlorovinyl ketones in particular react rapidly and in high yield. 2-Methylcyclohexenone has thereby been converted into a cis-dimethyl octalone; the conversion illustrates the effectiveness of β-chlorovinyl methyl ketone in the Robinson annelation. Reactions of the lithium enolate and titanium enol of 2,6- dimethylcyclohexanone with the β-substituted enones to give the corresponding unsaturated 1,5-dicarbonyl compounds and other products are also recorded.

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ChemInform Abstract: Synthesis of Clavulones (Claviridenones) via (3 + 2) Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone.

ChemInform ◽

10.1002/chin.199740286 ◽

2010 ◽

Vol 28 (40) ◽

pp. no-no

Author(s):

K. TAKEDA ◽

A. NAKAJIMA ◽

E. YOSHII

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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Discussion Addendum for: [3 + 4] Annulation Using a [β-(Trimethylsilyl) acryloyl]silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S)-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo [5.4.0]undec-4-en-2-one

Organic Syntheses ◽

10.15227/orgsyn.089.0267 ◽

2012 ◽

Vol 89 ◽

pp. 267 ◽

Cited By ~ 2

Keyword(s):

Methyl Ketone ◽

Lithium Enolate ◽

Alpha Beta

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[3 + 4] ANNULATION USING A [a-(TRIMETHYLSILYL)ACRYLOYL]SILANE AND THE LITHIUM ENOLATE OF AN b,b-UNSATURATED METHYL KETONE: (1R,6S,7S)-4-(tert-BUTYLDIMETHYLSILOXY)-6-(TRIMETHYLSILYL)BICYCLO[5.4.0]UNDEC-4-EN-2-ONE

Organic Syntheses ◽

10.15227/orgsyn.076.0199 ◽

1999 ◽

Vol 76 ◽

pp. 199 ◽

Cited By ~ 16

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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[3 + 4] Annulation Using a [β-(Trimethylsilyl)Acryloyl]Silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S*)-4-(Tert-Butyldimethylsiloxy)-6-(Trimethylsilyl)Bicyclo[5.4.0]Undec-4-En-2-One

Organic Syntheses ◽

10.1002/0471264180.os076.20 ◽

2003 ◽

pp. 199-199

Author(s):

Kei Takeda ◽

Akemi Nakajima ◽

Mika Takeda ◽

Eiichi Yoshii

Keyword(s):

Methyl Ketone ◽

Lithium Enolate

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The unexpected formation of a lithium-enolate from bis2-[(dimethylamino)methyl]phenyl copper lithium. X-ray structure of Li4[OC(CH2)C6H4CH2NMe2-2]4

Journal of Organometallic Chemistry ◽

10.1016/0022-328x(85)80217-5 ◽

1985 ◽

Vol 292 (3) ◽

pp. 319-324 ◽

Cited By ~ 17

Author(s):

Johann T.B.H. Jastrzebski ◽

Gerard Van Koten ◽

Martin J.N. Christophersen ◽

Casper H. Stam

Keyword(s):

Unexpected Formation ◽

X Ray ◽

Lithium Enolate ◽

Methyl Phenyl

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Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenyl propanal: enthalpy and entropy contribution

Tetrahedron Letters ◽

10.1016/s0040-4039(01)01320-x ◽

2001 ◽

Vol 42 (42) ◽

pp. 7383-7385 ◽

Cited By ~ 9

Author(s):

Gianfranco Cainelli ◽

Paola Galletti ◽

Daria Giacomini ◽

Paolo Orioli

Keyword(s):

Temperature Effect ◽

Butyl Acetate ◽

Aldol Condensation ◽

Tert Butyl ◽

Entropy Contribution ◽

Lithium Enolate ◽

Enthalpy And Entropy

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Ternary vapour-liquid equilibria system: Acetoneethyl methyl ketone-cyclohexane

Journal of Applied Chemistry ◽

10.1002/jctb.5010071003 ◽

2007 ◽

Vol 7 (10) ◽

pp. 535-543

Author(s):

K. V. Kurmanadha Rao ◽

V. V. G. Krishnamurty ◽

C. Venkata Rao

Keyword(s):

Methyl Ketone

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Synthesis of the Lithium Enolate of (S)-(+)-sec-Butyl Methyl Ketone and Formation of Chiral 1,3-Diketones by Acylation

Discussion Addendum for: [3 + 4] Annulation Using a [β-(Trimethylsilyl) acryloyl]silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S)-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo [5.4.0]undec-4-en-2-one

Synthesis of Clavulones (Claviridenones) via [3+2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone

Efficient Trapping of Ketone Enolates With Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-Sulfinyl- and β-Chloro-Vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds

ChemInform Abstract: Synthesis of Clavulones (Claviridenones) via (3 + 2) Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone.

Discussion Addendum for: [3 + 4] Annulation Using a [β-(Trimethylsilyl) acryloyl]silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S)-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo [5.4.0]undec-4-en-2-one

[3 + 4] ANNULATION USING A [a-(TRIMETHYLSILYL)ACRYLOYL]SILANE AND THE LITHIUM ENOLATE OF AN b,b-UNSATURATED METHYL KETONE: (1R,6S,7S)-4-(tert-BUTYLDIMETHYLSILOXY)-6-(TRIMETHYLSILYL)BICYCLO[5.4.0]UNDEC-4-EN-2-ONE

[3 + 4] Annulation Using a [β-(Trimethylsilyl)Acryloyl]Silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R*,6S*,7S*)-4-(Tert-Butyldimethylsiloxy)-6-(Trimethylsilyl)Bicyclo[5.4.0]Undec-4-En-2-One

The unexpected formation of a lithium-enolate from bis2-[(dimethylamino)methyl]phenyl copper lithium. X-ray structure of Li4[OC(CH2)C6H4CH2NMe2-2]4

Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenyl propanal: enthalpy and entropy contribution

Ternary vapour-liquid equilibria system: Acetoneethyl methyl ketone-cyclohexane

[3 + 4] Annulation Using a [β-(Trimethylsilyl)Acryloyl]Silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S*)-4-(Tert-Butyldimethylsiloxy)-6-(Trimethylsilyl)Bicyclo[5.4.0]Undec-4-En-2-One