2003
DOI: 10.5059/yukigoseikyokaishi.61.1088
|View full text |Cite
|
Sign up to set email alerts
|

Cyclization, Ring-Expansion, and Several Cascade Reactions Utilizing Allenylic Molecular Structure Characteristics

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
6
0

Year Published

2004
2004
2013
2013

Publication Types

Select...
7

Relationship

2
5

Authors

Journals

citations
Cited by 8 publications
(6 citation statements)
references
References 5 publications
0
6
0
Order By: Relevance
“…Speculative mechanisms for the Pd(0)- and phosphine-catalyzed ring-expansion reactions can be suggested on the basis of the experimental results described above (Figure ). 2f, In the first step of the catalytic cycle, the oxidative addition of the hydroxy group of 2a − d to a Pd(0) catalyst generates the complex A , 2f, in which the reductive elimination of the Pd(II) species, followed by migration of the C1−C2 bond in a concerted manner ( C ), may give the ring-expanded products 3a − d .
2 Plausible mechanisms for the Pd(0)- and phosphine-catalyzed ring-expansion reactions of 2a − d .
…”
mentioning
confidence: 97%
See 1 more Smart Citation
“…Speculative mechanisms for the Pd(0)- and phosphine-catalyzed ring-expansion reactions can be suggested on the basis of the experimental results described above (Figure ). 2f, In the first step of the catalytic cycle, the oxidative addition of the hydroxy group of 2a − d to a Pd(0) catalyst generates the complex A , 2f, in which the reductive elimination of the Pd(II) species, followed by migration of the C1−C2 bond in a concerted manner ( C ), may give the ring-expanded products 3a − d .
2 Plausible mechanisms for the Pd(0)- and phosphine-catalyzed ring-expansion reactions of 2a − d .
…”
mentioning
confidence: 97%
“…Ring-expansion reactions have provided chemists a considerably useful tool for the construction of various biologically active natural products and drugs . Recent efforts in our laboratory have focused on base-mediated and Pd(0)-catalyzed ring-expansion reactions (5 → 7 and 5 → 6) using various hydroxy allenyl cyclic compounds . Liebeskind and Stone3a and the Butenschön group 3b reported acid (CF 3 CO 2 H)-catalyzed ring-expansion reactions (4 → 5) of methoxyallenylcyclobutenols via corresponding enone intermediates, thus releasing four-membered ring strain 3a.…”
mentioning
confidence: 99%
“…Similar alkaline hydrolysis of 5a, b, d, and e with KOH also afforded the corresponding malonic half-esters, which were similarly decarboxylated by OH Ϫ to form in situ the acetylamino allenyl esters 8a, b, d, and e. Then, oxazole ring formation in the molecules 8 occurred via intramolecular 5-endo-mode cyclization. Thus, the overall reactions from 5a, b, d, and e to trisubstituted oxazoles 7a, b, d, and e proceeded in a cascade reaction manner, 28) as shown in Chart 3. The success of this intramolecular 5-endo-mode cyclization to give the trisubstituted oxazoles prompted us to develop various endo-mode carbocyclic and heterocyclic cyclization reactions by utilizing the conjugated allenyl ketone systems.…”
mentioning
confidence: 99%
“…27) We now describe, in detail, expeditious syntheses of conjugated allenyl esters and trisubstituted oxazoles and the related reactions based on the following concept and background. 28) Cysteine proteases of the papain family have been implicated in the pathogenesis of a various of serious diseases. Hence, the development of cysteine protease inhibitors has been extensively studied worldwide.…”
mentioning
confidence: 99%
See 1 more Smart Citation