Carbometalation of Vinyllithiums by Zincated Allyltrimethylsilane

Ferreira, Franck; Normant, Jean F.

doi:10.1002/1099-0690(200011)2000:21<3581::aid-ejoc3581>3.0.co;2-c

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Ii3 Heterosubstituted Allyl Zinc Reagents1

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2009

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Cited by 8 publications

(3 citation statements)

References 22 publications

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“…When 215 is added to 213, also in the presence of an excess of ZnBr 2 and MgBr 2 to speed up the reaction, the syn-isomer 216 is formed in 70 % yield (Scheme 7-128) [155].…”

Section: 182mentioning

confidence: 99%

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Carbometallation Reactions

Marek¹,

and²,

Banon-Tenne³

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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“…When 215 is added to 213, also in the presence of an excess of ZnBr 2 and MgBr 2 to speed up the reaction, the syn-isomer 216 is formed in 70 % yield (Scheme 7-128) [155].…”

Section: 182mentioning

confidence: 99%

“…A notable shortcoming is that alkyl Grignard reagents other than ethylmagnesium halides are less efficient or even fail to participate in catalytic carbomagnesiation. To address this problem, Scheme 7-128 Addition of metallated allylsilane to a g-alkoxyvinyllithium [155].…”

Section: 182mentioning

confidence: 99%

Carbometallation Reactions

Marek¹,

and²,

Banon-Tenne³

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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“…Protection of the alcohol by a MOM group is equally efficient and allows for easier deprotection. Thus, taking advantage of the silicon moiety, a new approach of serricornin has been developed 29 according to Scheme 14. Allyltrimethylsilane is deprotonated and mixed with the lithiated MOM ether derived from (Z)-1-iodopent-1-en-3-ol.…”

Section: Ii3 Heterosubstituted Allyl Zinc Reagentsmentioning

confidence: 99%

1,1-Dimetallic Reagents for the Elaboration of Stereoselectively Di- or Trisubstituted Linear Substrates

Normant

2001

Acc. Chem. Res.

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Although gem-dimetallic species have been known for a long time, and reacted once or twice with electrophiles, the allyl zincation of substituted vinyl metals has emerged as a particularly efficient access to such species. This is due to a high face selectivity, in the addition to the C=C bond, which can be governed by vicinal or more remote heteroatoms. This strategy has some aspects in common with the well-known allylations or aldol condensations to carbonyl derivatives. But in the present case, the C=C bond has a low polarity. We present here some examples which lead to di- or polysubstituted linear substrates, of given geometry, where the organodimetallic obtained has been doubly protonated by water. Further elaborations (to alkenes, ketones, etc.) are possible.

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1,1‐Bismetallated Species

Matsubara

2009

Patai's Chemistry of Functional Groups

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Introduction Preparation of sp 3 ‐Geminated Organodizinc Reagents Reaction of sp 3 ‐Geminated Organodizinc Reagents Preparation and Reaction of sp 2 ‐Geminated Organodizinc Reagents Conclusion

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Carbometalation of Vinyllithiums by Zincated Allyltrimethylsilane

Abstract: The addition of zincated allytrimethylsilane to γ‐alkoxyvinyllithiums in the presence of an excess of ZnBr2 (and MgBr2) is highly diastereoselective when performed under precise temperature conditions. A formal synthesis of serricornin is proposed.

Cited by 8 publications

References 22 publications

Carbometallation Reactions

Carbometallation Reactions

1,1-Dimetallic Reagents for the Elaboration of Stereoselectively Di- or Trisubstituted Linear Substrates

1,1‐Bismetallated Species

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