Based on the following reaction, the resolution step provides a maximum theoretical yield of alcohol (S)-2 of 50%. This is a limitation of the use of kinetic resolutions in organic synthesis. Need help providing an alternate way to prepare enantioenriched alcohol (S)-2 that can provide greater than 50% theoretical yield.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question

Based on the following reaction, the resolution step provides a maximum theoretical yield of alcohol (S)-2 of 50%. This is a limitation of the use of kinetic resolutions in organic synthesis. Need help providing an alternate way to prepare enantioenriched alcohol (S)-2 that can provide greater than 50% theoretical yield. 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
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 3 images

Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY