Skip to main content
. Author manuscript; available in PMC: 2010 Apr 14.
Published in final edited form as: Adv Synth Catal. 2009 Nov;351(17):2976–2990. doi: 10.1002/adsc.200900603

Table 4.

pH dependence for the reduction of ketoisophorone 3a with 0.02 μM PETNR.[a]

Entry pH Conv.
(1.5 h)[b]
[%]
Yield
(1.5 h)[b]
[%]
ee
(1.5 h)[c]
[%]
ee
(24 h)[c]
[%]
1 5.0 2 1 >99 93
2 5.5 5 3 >99 93
3 6.0 13 12 >99 91
4 6.5 24 22 >99 87
5 7.0 27 26 99 79
6 7.5 28 27 98 62
7 8.0 33 31 97 41
8 8.5 32 31 95 13
9 9.0 31 30 92 0
[a]

Conditions: The reactions contained Bis-Tris/HEPPS/CHES buffer (75 mM/38 mM/38 mM, respectively, 1 mL total volume), alkene 3a (5 mM), PETNR (0.02 μM), and NADPH (6 mM). Reactions were agitated at 30 °C at 130 rpm for 1.5 and 24 h. Alkene 3a was added as a DMF solution (2% final DMF concentration).

[b]

By GC using a DB-Wax column.

[c]

By GC using Chirasil-DEX-CB column.