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. 2019 Oct 18;10(48):11141–11146. doi: 10.1039/c9sc04752b

Table 3. Completing the flow synthesis of 1: Optimization of the BH3·DMS-mediated amide/ester reduction.

Inline graphic
# a Flow rate (μL min–1)
3/BH3·DMS ratio Conv. b (%) Chemosel. b , c (%)
P1 P2
1 d 200 200 e 1 : 10 96 74
2 100 100 f 1 : 10 100 100
3 130 70 f 1 : 5.4 100 100
4 140 60 f 1 : 4.3 100 95
5 150 50 f 1 : 3.3 99 76
6 260 140 e 1 : 5.4 100 100
7 390 210 g 1 : 5.4 100 93

a95-96% ee was measured in all reactions (by using chiral HPLC).

bDetermined by 1H-NMR analysis of the crude product.

c 1a formed as minor product in entries 1, 4, 5 and 7.

dAt 50 °C.

e t r= 30 min.

f t r= 60 min.

g t r= 20 min.