Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand

Tatsuyuki Tsubo, Hsiu Hui Chen, Minako Yokomori, Kosuke Fukui, Satoshi Kikuchi, Tohru Yamada

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.

Original languageEnglish
Pages (from-to)780-782
Number of pages3
JournalChemistry Letters
Volume41
Issue number8
DOIs
Publication statusPublished - 2012

Fingerprint

Borohydrides
Ketones
Ligands
Cobalt
Enantioselectivity
Chloroform
Alcohols
Derivatives
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand. / Tsubo, Tatsuyuki; Chen, Hsiu Hui; Yokomori, Minako; Fukui, Kosuke; Kikuchi, Satoshi; Yamada, Tohru.

In: Chemistry Letters, Vol. 41, No. 8, 2012, p. 780-782.

Research output: Contribution to journalArticle

Tsubo, Tatsuyuki ; Chen, Hsiu Hui ; Yokomori, Minako ; Fukui, Kosuke ; Kikuchi, Satoshi ; Yamada, Tohru. / Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand. In: Chemistry Letters. 2012 ; Vol. 41, No. 8. pp. 780-782.
@article{ed670a47fc2d42b4a7b349ac54cf5f13,
title = "Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand",
abstract = "For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.",
author = "Tatsuyuki Tsubo and Chen, {Hsiu Hui} and Minako Yokomori and Kosuke Fukui and Satoshi Kikuchi and Tohru Yamada",
year = "2012",
doi = "10.1246/cl.2012.780",
language = "English",
volume = "41",
pages = "780--782",
journal = "Chemistry Letters",
issn = "0366-7022",
publisher = "Chemical Society of Japan",
number = "8",

}

TY - JOUR

T1 - Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand

AU - Tsubo, Tatsuyuki

AU - Chen, Hsiu Hui

AU - Yokomori, Minako

AU - Fukui, Kosuke

AU - Kikuchi, Satoshi

AU - Yamada, Tohru

PY - 2012

Y1 - 2012

N2 - For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.

AB - For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.

UR - http://www.scopus.com/inward/record.url?scp=84864455943&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84864455943&partnerID=8YFLogxK

U2 - 10.1246/cl.2012.780

DO - 10.1246/cl.2012.780

M3 - Article

VL - 41

SP - 780

EP - 782

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 8

ER -