Homa Sadeghzadeh 02-15-2020...Step 9: Prins Cyclization, WagnerMeerwein- rearrangemnt. …

22
Homa Sadeghzadeh 02-15-2020 1

Transcript of Homa Sadeghzadeh 02-15-2020...Step 9: Prins Cyclization, WagnerMeerwein- rearrangemnt. …

Homa Sadeghzadeh02-15-2020

1

2

Reagents:

3

Presenter
Presentation Notes
1,3-cyclohexanedione

Step 1:

4

Presenter
Presentation Notes
lipase acrylic resin , vinyl acetate

Step 2:

https://sites.google.com/site/mechanismmordor/2nd-year-mechanisms/nucelophilic-addition/sculponeatin-n/question-1-answer?tmpl=%2Fsystem%2Fapp%2Ftemplates%2Fprint%2F&showPrintDialog=1 5

Step 3:

6

Presenter
Presentation Notes
Metal exchange

Step 4:

7

Presenter
Presentation Notes
Diels alder

Step 5:

8

Presenter
Presentation Notes
Methoxy methyl

Step 6:

9

Step 7:

10

Step 8:

11

Presenter
Presentation Notes
Thionyl chloride

Step 9:

Prins Cyclization, Wagner-Meerwein rearrangemnt

https://cheminfographic.wordpress.com/2017/12/02/53-wagner-meerwein-rearrangement-1899-1914/12

Step 10:

https://en.chem-station.com/reactions-2/2016/03/mukaiyama-hydration.html

Ruthenium Oxidation Complexes pp 1-134, William P. Griffith 13

Presenter
Presentation Notes
Phenylsilane,

Step 11:

14

Step 12:

15

Step 13:

https://en.wikipedia.org/wiki/Riley_oxidation

Riley, Harry Lister; Morley, John Frederick; Friend, Norman Alfred Child (1932-01-01). "255. Selenium dioxide, a new oxidising agent. Part I. Its reaction with aldehydes and ketones". Journal of the Chemical Society (Resumed). 0: 1875–1883. 16

Step 14:

17

Step 15:

18

Presenter
Presentation Notes
Hydroxyl amine

Step 16:

19

Presenter
Presentation Notes
Reduction of Oxime to amine and then amine react with carbonyl

Step 17:

20

Step 18:

21

Thanks!

22