Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi, Kiitiro Utimoto

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent.

Original languageEnglish
Pages (from-to)5263-5266
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number29
DOIs
Publication statusPublished - Jul 18 1994
Externally publishedYes

Fingerprint

Stereoselectivity
Ketones
Isomers
lithium aluminum hydride
tetrahydrofuran
diisobutylaluminum

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{89446f9377004f91888d531383b2de2b,
title = "Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols",
abstract = "The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent.",
author = "Takashi Ishihara and Koichi Yamaguchi and Manabu Kuroboshi and Kiitiro Utimoto",
year = "1994",
month = "7",
day = "18",
doi = "10.1016/S0040-4039(00)77080-8",
language = "English",
volume = "35",
pages = "5263--5266",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "29",

}

TY - JOUR

T1 - Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

AU - Ishihara, Takashi

AU - Yamaguchi, Koichi

AU - Kuroboshi, Manabu

AU - Utimoto, Kiitiro

PY - 1994/7/18

Y1 - 1994/7/18

N2 - The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent.

AB - The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent.

UR - http://www.scopus.com/inward/record.url?scp=0028237288&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028237288&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)77080-8

DO - 10.1016/S0040-4039(00)77080-8

M3 - Article

VL - 35

SP - 5263

EP - 5266

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -