Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

Nan Young Jeon; Sung Jin Ko; Keehoon Won; Han Young Kang; Bum Tae Kim; Yeon Soo Lee; Hyuk Lee

doi:10.1016/j.tetlet.2006.07.034

Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

Nan Young Jeon, Sung Jin Ko, Keehoon Won, Han Young Kang, Bum Tae Kim, Yeon Soo Lee, Hyuk Lee

Department of Chemical and Biochemical Engineering

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

20 Scopus citations

Abstract

Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.

Original language	English
Pages (from-to)	6517-6520
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.034
State	Published - 11 Sep 2006

Keywords

Alkyl lactate
Alkyl O-lactyllactate
Kinetic resolution
Novozym 435
rac-Lactide

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10.1016/j.tetlet.2006.07.034

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title = "Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435",

abstract = "Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.",

keywords = "Alkyl lactate, Alkyl O-lactyllactate, Kinetic resolution, Novozym 435, rac-Lactide",

author = "Jeon, {Nan Young} and Ko, {Sung Jin} and Keehoon Won and Kang, {Han Young} and Kim, {Bum Tae} and Lee, {Yeon Soo} and Hyuk Lee",

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language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

AU - Jeon, Nan Young

AU - Ko, Sung Jin

AU - Won, Keehoon

AU - Kang, Han Young

AU - Kim, Bum Tae

AU - Lee, Yeon Soo

AU - Lee, Hyuk

PY - 2006/9/11

Y1 - 2006/9/11

N2 - Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.

AB - Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.

KW - Alkyl lactate

KW - Alkyl O-lactyllactate

KW - Kinetic resolution

KW - Novozym 435

KW - rac-Lactide

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U2 - 10.1016/j.tetlet.2006.07.034

DO - 10.1016/j.tetlet.2006.07.034

M3 - Article

AN - SCOPUS:33746799705

SN - 0040-4039

VL - 47

SP - 6517

EP - 6520

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

Abstract

Keywords

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