Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl

Kazuhiko Takai, Ryotaro Morita, Chika Toratsu

Research output: Contribution to journal › Article

36 Citations (Scopus)

Abstract

Efficient trapping of chromium enolates in the presence of Et3SiCl gives silyl enol ethers. This trapping changes the course of the reaction between α,β-unsaturated ketones and aldehydes from a sequential aldol-cyclopropanol formation to a cross pinacol-type coupling reaction (Eq. (1); for example, R1=n-C8H17,R2=Ph(CH2) 2]. The antilsyn ratios of the 1,2-diols depend on the reaction temperature.

Original languageEnglish
Pages (from-to)1116-1119
Number of pages4
JournalAngewandte Chemie - International Edition
Volume40
Issue number6
DOIs
Publication statusPublished - Mar 14 2001

Fingerprint

Ethers
Chromium
Ketones
Aldehydes
Temperature
cyclopropanol
3-hydroxybutanal

Keywords

  • Aldehydes
  • Chromium
  • Diols
  • Ketones
  • Pinacol coupling

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. / Takai, Kazuhiko; Morita, Ryotaro; Toratsu, Chika.

In: Angewandte Chemie - International Edition, Vol. 40, No. 6, 14.03.2001, p. 1116-1119.

Research output: Contribution to journal › Article

Takai, K, Morita, R & Toratsu, C 2001, 'Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl', Angewandte Chemie - International Edition, vol. 40, no. 6, pp. 1116-1119. https://doi.org/10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T
Takai K, Morita R, Toratsu C. Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. Angewandte Chemie - International Edition. 2001 Mar 14;40(6):1116-1119. https://doi.org/10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T
Takai, Kazuhiko ; Morita, Ryotaro ; Toratsu, Chika. / Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. In: Angewandte Chemie - International Edition. 2001 ; Vol. 40, No. 6. pp. 1116-1119.
@article{e721cd59ea914133b980b94646672db7,
title = "Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl",
abstract = "Efficient trapping of chromium enolates in the presence of Et3SiCl gives silyl enol ethers. This trapping changes the course of the reaction between α,β-unsaturated ketones and aldehydes from a sequential aldol-cyclopropanol formation to a cross pinacol-type coupling reaction (Eq. (1); for example, R1=n-C8H17,R2=Ph(CH2) 2]. The antilsyn ratios of the 1,2-diols depend on the reaction temperature.",
keywords = "Aldehydes, Chromium, Diols, Ketones, Pinacol coupling",
author = "Kazuhiko Takai and Ryotaro Morita and Chika Toratsu",
year = "2001",
month = "3",
day = "14",
doi = "10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T",
language = "English",
volume = "40",
pages = "1116--1119",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "6",

}

TY - JOUR

T1 - Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl

AU - Takai, Kazuhiko

AU - Morita, Ryotaro

AU - Toratsu, Chika

PY - 2001/3/14

Y1 - 2001/3/14

N2 - Efficient trapping of chromium enolates in the presence of Et3SiCl gives silyl enol ethers. This trapping changes the course of the reaction between α,β-unsaturated ketones and aldehydes from a sequential aldol-cyclopropanol formation to a cross pinacol-type coupling reaction (Eq. (1); for example, R1=n-C8H17,R2=Ph(CH2) 2]. The antilsyn ratios of the 1,2-diols depend on the reaction temperature.

AB - Efficient trapping of chromium enolates in the presence of Et3SiCl gives silyl enol ethers. This trapping changes the course of the reaction between α,β-unsaturated ketones and aldehydes from a sequential aldol-cyclopropanol formation to a cross pinacol-type coupling reaction (Eq. (1); for example, R1=n-C8H17,R2=Ph(CH2) 2]. The antilsyn ratios of the 1,2-diols depend on the reaction temperature.

KW - Aldehydes

KW - Chromium

KW - Diols

KW - Ketones

KW - Pinacol coupling

UR - http://www.scopus.com/inward/record.url?scp=0035857574&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035857574&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T

DO - 10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T

M3 - Article

AN - SCOPUS:0035857574

VL - 40

SP - 1116

EP - 1119

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 6

ER -

Access to Document