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

Kazuhiko Takai; Ryotaro Morita; Chika Toratsu

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

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 › peer-review

38 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 language	English
Pages (from-to)	1116-1119
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	6
DOIs	https://doi.org/10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T
Publication status	Published - Mar 14 2001

Keywords

Aldehydes
Chromium
Diols
Ketones
Pinacol coupling

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

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

Cite this

@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 = mar,

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 -