Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

被引：38

作者：

Cosgrove, Sebastian C. ^{[1
,2
,3
]}

Hussain, Shahed ^{[1
,4
]}

Turner, Nicholas J. ^{[1
]}

Marsden, Stephen P. ^{[2
,3
]}

机构：

[1] Univ Manchester, Manchester Inst Biotechnol, Sch Chem, 131 Princess St, Manchester M1 7DN, Lancs, England

[2] Univ Leeds, Inst Proc Res & Dev, Leeds LS2 9JT, W Yorkshire, England

[3] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[4] Dr Reddys Labs, Cambridge Sci Pk,Milton Rd, Cambridge CB4 0WW, England

来源：

ACS CATALYSIS | 2018年 / 8卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

rhodium catalysis; biocatalysis; amine oxidase; alkaloidal tetrahydroquinoline; enzymatic deracemization; IMINE REDUCTASES IREDS; CYCLOHEXYLAMINE OXIDASE; AMINE OXIDASE; AQUEOUS-MEDIA; NITROGEN-HETEROCYCLES; ASYMMETRIC-SYNTHESIS; MONOAMINE OXIDASES; CHIRAL AMINES; DERACEMIZATION; ENZYME;

D O I：

10.1021/acscatal.8b01220

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

引用

页码：5570 / 5573

页数：7

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