Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives

Jing Nan Cui; Ryoji Teraoka; Tadashi Ema; Takashi Sakai; Masanori Utaka

doi:10.1016/S0040-4039(97)00524-8

Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives

Jing Nan Cui, Ryoji Teraoka, Tadashi Ema, Takashi Sakai, Masanori Utaka

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

18 Citations (Scopus)

Abstract

Bakers' yeast reduction of 1-chloro-2,4-alkanediones 1a afforded 1-chloro-2-hydroxy-4-alkanones 2a regioselectively with low optical purities. Application of inhibitors and heat-treatment of bakers' yeast enhanced the optical purities toward the S enantiomer (88-91% ee). Organic solvents added in small amounts were also found to enhance the S selectivity significantly. High optical purities 94-96% ee were achieved by the combined action of the inhibitor, heat-treatment, and organic solvent.

Original language	English
Pages (from-to)	3021-3024
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(97)00524-8
Publication status	Published - Apr 28 1997

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(97)00524-8

Cite this

@article{edea9e93056d4901bd04fbab679c70e8,

title = "Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives",

abstract = "Bakers' yeast reduction of 1-chloro-2,4-alkanediones 1a afforded 1-chloro-2-hydroxy-4-alkanones 2a regioselectively with low optical purities. Application of inhibitors and heat-treatment of bakers' yeast enhanced the optical purities toward the S enantiomer (88-91% ee). Organic solvents added in small amounts were also found to enhance the S selectivity significantly. High optical purities 94-96% ee were achieved by the combined action of the inhibitor, heat-treatment, and organic solvent.",

author = "Cui, {Jing Nan} and Ryoji Teraoka and Tadashi Ema and Takashi Sakai and Masanori Utaka",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan. We are grateful to the SC-NMR Laboratory of Okayama University for the measurement of NMR spectra.",

year = "1997",

month = apr,

day = "28",

doi = "10.1016/S0040-4039(97)00524-8",

language = "English",

volume = "38",

pages = "3021--3024",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "17",

}

TY - JOUR

T1 - Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast

T2 - Effects of organic solvents as additives

AU - Cui, Jing Nan

AU - Teraoka, Ryoji

AU - Ema, Tadashi

AU - Sakai, Takashi

AU - Utaka, Masanori

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan. We are grateful to the SC-NMR Laboratory of Okayama University for the measurement of NMR spectra.

PY - 1997/4/28

Y1 - 1997/4/28

N2 - Bakers' yeast reduction of 1-chloro-2,4-alkanediones 1a afforded 1-chloro-2-hydroxy-4-alkanones 2a regioselectively with low optical purities. Application of inhibitors and heat-treatment of bakers' yeast enhanced the optical purities toward the S enantiomer (88-91% ee). Organic solvents added in small amounts were also found to enhance the S selectivity significantly. High optical purities 94-96% ee were achieved by the combined action of the inhibitor, heat-treatment, and organic solvent.

AB - Bakers' yeast reduction of 1-chloro-2,4-alkanediones 1a afforded 1-chloro-2-hydroxy-4-alkanones 2a regioselectively with low optical purities. Application of inhibitors and heat-treatment of bakers' yeast enhanced the optical purities toward the S enantiomer (88-91% ee). Organic solvents added in small amounts were also found to enhance the S selectivity significantly. High optical purities 94-96% ee were achieved by the combined action of the inhibitor, heat-treatment, and organic solvent.

UR - http://www.scopus.com/inward/record.url?scp=0030966753&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030966753&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)00524-8

DO - 10.1016/S0040-4039(97)00524-8

M3 - Article

AN - SCOPUS:0030966753

VL - 38

SP - 3021

EP - 3024

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -

Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this