Organic Letters
Organic Letters
5 years ago

Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines

Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines
Jian-He Xu, Hao Li, Gao-Wei Zheng, Ping Tian
A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L–1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01274

DOI: 10.1021/acs.orglett.7b01274

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