2009
DOI: 10.1021/ja900946h
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Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides

Abstract: A new rhodium-catalyzed carbozincation of ynamides has been developed, using diorganozinc reagents or functionalized alkylzinc halides. The reactions are highly regio- and stereoselective, allowing access to a wide range of multisubstituted enamides, which are increasingly important building blocks for organic synthesis. Utilization of the alkenylzinc intermediates in further carbon-carbon bond-forming reactions to form trisubstituted enamides is also possible.

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Cited by 142 publications
(40 citation statements)
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“…24b The alternative hydroamidation of terminal alkynes for the synthesis of Z-enamides has not been applied to propenyl systems. 11 …”
Section: Resultsmentioning
confidence: 99%
“…24b The alternative hydroamidation of terminal alkynes for the synthesis of Z-enamides has not been applied to propenyl systems. 11 …”
Section: Resultsmentioning
confidence: 99%
“…On hydrolysis, this aldol surrogate quantitatively furnishes the aldol derivatives 381 as single isomers [110]. An efficient protocol enabling the carbometallation of ynamides with organozinc reagents to be performed in a catalytic manner was described recently by Gourdet and Lam [111]. This new protocol employed the Rh(cod)(acac) complex as a catalyst and diorganozinc reagents (Scheme 10.130).…”
Section: Carbometallation Of Alkynes 845mentioning
confidence: 99%
“…R 1 = Ph(CH 2 ) 2 ; TBSO(CH 2 ) 2 ; n -C 6 H 13 ; PhR 1 = Me, Et, n -Bu, vinyl, p -FC 6 H 4 , p -MeOC 6 H 4 , 2-thiophenyl, X = CH 2 , MeN, O *Scheme 10.130Rhodium-catalyzed carbozincation of ynamides[111].…”
mentioning
confidence: 99%
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“…Based on our recent interest in the chemistry of ynamides [718] and inspired by recent reports from Meyer and Cossy [1921], Marek [2224] and Lam [2526] on their carbopalladation, carbocupration and carbozincation, respectively, we decided to study the intramolecular carbolithiation of ynamides, which may provide an interesting entry to highly functionalized 1,4-dihydropyridines [2729] and pyridines [30–33], most useful building blocks in organic synthesis and medicinal chemistry as well. Our strategy is summarized in Scheme 1 and is based on the following assumptions: According to the remarkable work of the Beak group on the α-lithiation of Boc-protected amines [3438], N -allyl-ynamides 1 should be readily deprotonated to afford a transient chelation-stabilized allyllithium 2 and, provided that a metallotropic equilibrium exists between this intermediate and the less-stable allyllithium 3 , an intramolecular carbometallation may then occur to yield a chelation-stabilized vinyllithium 4 and drive the overall process to the formation of the heterocyclic ring system.…”
Section: Introductionmentioning
confidence: 99%