Considering the following reaction, while kinetic resolutions limit your yield of, for example, acetate 3 to 50%, in certain cases this can be improved by using a sequence of reactions that convert the undesired enantiomer to the desired one. Propose a series of such reactions that would allow you to convert the (S)-2 to acetate 3. Thank you :)

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.51P
icon
Related questions
Question

Considering the following reaction, while kinetic resolutions limit your yield of, for example, acetate 3 to 50%, in certain cases this can be improved by using a sequence of reactions that convert the undesired enantiomer to the desired one. Propose a series of such reactions that would allow you to convert the (S)-2 to acetate 3. Thank you :)

 

-CO̟Et
OAc
-co,Et
OCH3
(i) dil aq. HCI, 70 °C
Lipase PS,
t-BUOCH3, 168 h
OH
он (S)-2
(iї) K-СОз, 168 h
OCH3
-CO2Et
1
CO̟Et
Eto-P
EtO
ОН
ОАс 3
(R/S)-2
Figure 2.2: Synthesis of (R/S)-2 and kinetic resolution with lipase PS.
Transcribed Image Text:-CO̟Et OAc -co,Et OCH3 (i) dil aq. HCI, 70 °C Lipase PS, t-BUOCH3, 168 h OH он (S)-2 (iї) K-СОз, 168 h OCH3 -CO2Et 1 CO̟Et Eto-P EtO ОН ОАс 3 (R/S)-2 Figure 2.2: Synthesis of (R/S)-2 and kinetic resolution with lipase PS.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning