Fischer‐Type Carbene Complexes

Dötz, Karl Heinz; Minatti, Ana

doi:10.1002/9783527619399.ch3a

Transition Metals for Organic Synthesis 1998

DOI: 10.1002/9783527619399.ch3a

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Fischer‐Type Carbene Complexes

Karl Heinz Dötz¹,

Ana Minatti²

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Cited by 2 publications

References 156 publications

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From α,β‐Unsaturated Fischer Carbene Complexes to Highly Substituted 3‐Ethoxycyclopentadienes, Masked Cyclopentenones

Flynn

Schirmer

et al. 2004

Eur J Org Chem

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The β-amino-substituted α,β-unsaturated Fischer carbene complexes 3 are readily available by a four step one-pot procedure from terminal alkynes, chromium hexacarbonyl and secondary amines (24 examples with yields of 68−99% and 7 examples with yields of 26−63%). The formal [3+2] cycloadditions of complexes 3 with different alkynes including diynes and enynes performed in donor solvents such as pyridine or acetonitrile afforded highly substituted 5-(dialkylamino)-3-ethoxycyclopentadienes 7, generally in medium to excellent yields (25 examples with yields of 60−95% and 7 examples with yields of 18−53%). The steric and electronic effects of the substituents on the carbene complexes and the incorporated alkynes on the regio-and stereoselectivity of the ring-forming reaction have been elaborated. An interesting 1,5-or, more likely, 1,2-migration of the dimethylamino group was observed for 5-(dimethylamino)-3-ethoxycyclopentadienes with trimethylsilyl and iPr substituents at C-5. Attempted asymmetric syntheses of cyclopentadienes 7 from complexes 3 with chiral amino groups or substituents were only moderately successful. At a center of chirality in the secondary amino group, complexes of type 3 gave compounds 7 with diastereomeric excesses of, at best, 59% in yields of

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From α,β‐Unsaturated Fischer Carbene Complexes to Highly Substituted 3‐Ethoxycyclopentadienes, Masked Cyclopentenones

Flynn

Schirmer

et al. 2004

Eur J Org Chem

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Metallorganisch modifizierte Zucker. 26 [1] L.Iminoglycosyliden‐Komplexe — eine flexible metallorganische Route zu variabel funktionalisierten L.Iminozuckerderivaten

Jäkel¹,

Dötz²

2003

Zeitschrift anorg allge chemie

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Organometallic Modified Sugars. 26. L.Iminoglycosylidene Complexes — A Flexible Organometallic Route to Variably Functionalized L.Iminosugar Derivatives A straightforward two‐step chromium carbene strategy has been designed for the synthesis of L.iminopyranosylidene complexes from stannylated glycals based on a transmetalation for the introduction of a pentacarbonylchromium moiety via a vinyl chromate intermediate. The synthetic utility of these novel organometallic sugars is demonstrated by a convenient deprotonation/demetalation protocol to afford cyclic enamides as valuable functionalized carbohydrate building blocks.

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Fischer‐Type Carbene Complexes

Cited by 2 publications

References 156 publications

From α,β‐Unsaturated Fischer Carbene Complexes to Highly Substituted 3‐Ethoxycyclopentadienes, Masked Cyclopentenones

From α,β‐Unsaturated Fischer Carbene Complexes to Highly Substituted 3‐Ethoxycyclopentadienes, Masked Cyclopentenones

Metallorganisch modifizierte Zucker. 26 [1] L.Iminoglycosyliden‐Komplexe — eine flexible metallorganische Route zu variabel funktionalisierten L.Iminozuckerderivaten

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