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

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

Access to Document

10.1016/j.tetlet.2006.07.034

Cite this

@article{14cd063af8c948dd8f5d2ce506b09e36,

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 O-lactyllactate, Alkyl lactate, 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",

year = "2006",

month = sep,

day = "11",

doi = "10.1016/j.tetlet.2006.07.034",

language = "English",

volume = "47",

pages = "6517--6520",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "37",

}

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 O-lactyllactate

KW - Alkyl lactate

KW - Kinetic resolution

KW - Novozym 435

KW - rac-Lactide

UR - https://www.scopus.com/pages/publications/33746799705

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

Access to Document

Other files and links

Fingerprint

Cite this