Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol

Wei Ding; Mingze Li; Rongji Dai; Yulin Deng

doi:10.1016/j.tetasy.2012.09.009

Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol

Wei Ding, Mingze Li, Rongji Dai, Yulin Deng^*

^*Corresponding author for this work

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

An efficient chemoenzymatic route for the synthesis of enantiopure (R)-salsolinol through the use of Candida antarctica lipase A (CALA) was developed. Different parameters, including the acyl agent, the solvent, the temperature, and the amount of enzyme and substrates used, were investigated in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. The combination of CALA with phenyl allyl carbonates in toluene allowed the isolation of amines with high conversion (50%) and ee (98%) values.

Original language	English
Pages (from-to)	1376-1379
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	23
Issue number	18-19
DOIs	https://doi.org/10.1016/j.tetasy.2012.09.009
Publication status	Published - 15 Oct 2012

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title = "Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol",

abstract = "An efficient chemoenzymatic route for the synthesis of enantiopure (R)-salsolinol through the use of Candida antarctica lipase A (CALA) was developed. Different parameters, including the acyl agent, the solvent, the temperature, and the amount of enzyme and substrates used, were investigated in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. The combination of CALA with phenyl allyl carbonates in toluene allowed the isolation of amines with high conversion (50\%) and ee (98\%) values.",

author = "Wei Ding and Mingze Li and Rongji Dai and Yulin Deng",

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T1 - Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol

AU - Ding, Wei

AU - Li, Mingze

AU - Dai, Rongji

AU - Deng, Yulin

PY - 2012/10/15

Y1 - 2012/10/15

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AB - An efficient chemoenzymatic route for the synthesis of enantiopure (R)-salsolinol through the use of Candida antarctica lipase A (CALA) was developed. Different parameters, including the acyl agent, the solvent, the temperature, and the amount of enzyme and substrates used, were investigated in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. The combination of CALA with phenyl allyl carbonates in toluene allowed the isolation of amines with high conversion (50%) and ee (98%) values.

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U2 - 10.1016/j.tetasy.2012.09.009

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EP - 1379

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 18-19

ER -

Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol

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