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.

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
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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.
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