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9.2 Enzyme-Catalyzed Stereoselective Reactions in Continuous-Flow Systems 205

O OH OH
(S) (S)
HLADH +
(S) (R)
O O O

1 (S,S)-2 (fast) (S,R)-2 (slow)

NH 2 O 2 ATR NH 2 O
+
COOH DAAO (S) COOH COOH
3 L-4

O OH O
(S)
TADH (S) + (R)

5 (S,S)-6 (R)-5

Organic HO CN
a Ph
R H
O Aqueous b p-MeOC H 4
6
(R)-PaHNL (R)-8a–d
R H HCN H 3 PO 4 c Thiophen-2-yl
(S)-HbHNL
7a–d Aqueous
HO CN O
d
Organic R H O
(S)-8a–d
O
OH
HOOC O
9 OH
TK HO
OH 11
HO CHO
10
NH 2
TAM OH
HO
O
NH 2 OH 12

Figure 9.2 Stereoselective enzyme reactions in continuous-flow systems.