Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

Takashi Okazoe; Kazuhiko Takai; Koichiro Oshima; Kiitiro Utimoto

doi:10.1021/jo00228a055

Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr₂, Zn, TiCl₄, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

Takashi Okazoe, Kazuhiko Takai, Koichiro Oshima, Kiitiro Utimoto

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

131 Citations (Scopus)

Abstract

Reagents prepared by reduction of 1,1-di-bromoalkanes (R³CHBr₂) with zinc and TiCl₄in the presence of N,N,N,ʹNʹ-tetramethylethylenediamine in THF are effective in the conversion of esters (R¹CO₂R²) to the corresponding alkenyl ethers (R¹(R²O)C═CHR³) with high Z selectivity.

Original language	English
Pages (from-to)	4410-4412
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	52
Issue number	19
DOIs	https://doi.org/10.1021/jo00228a055
Publication status	Published - Sept 1 1987
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers",

abstract = "Reagents prepared by reduction of 1,1-di-bromoalkanes (R3CHBr2) with zinc and TiCl4in the presence of N,N,N,ʹNʹ-tetramethylethylenediamine in THF are effective in the conversion of esters (R1CO2R2) to the corresponding alkenyl ethers (R1(R2O)C═CHR3) with high Z selectivity.",

author = "Takashi Okazoe and Kazuhiko Takai and Koichiro Oshima and Kiitiro Utimoto",

year = "1987",

month = sep,

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doi = "10.1021/jo00228a055",

language = "English",

volume = "52",

pages = "4410--4412",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

AU - Okazoe, Takashi

AU - Takai, Kazuhiko

AU - Oshima, Koichiro

AU - Utimoto, Kiitiro

PY - 1987/9/1

Y1 - 1987/9/1

N2 - Reagents prepared by reduction of 1,1-di-bromoalkanes (R3CHBr2) with zinc and TiCl4in the presence of N,N,N,ʹNʹ-tetramethylethylenediamine in THF are effective in the conversion of esters (R1CO2R2) to the corresponding alkenyl ethers (R1(R2O)C═CHR3) with high Z selectivity.

AB - Reagents prepared by reduction of 1,1-di-bromoalkanes (R3CHBr2) with zinc and TiCl4in the presence of N,N,N,ʹNʹ-tetramethylethylenediamine in THF are effective in the conversion of esters (R1CO2R2) to the corresponding alkenyl ethers (R1(R2O)C═CHR3) with high Z selectivity.

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U2 - 10.1021/jo00228a055

DO - 10.1021/jo00228a055

M3 - Letter

AN - SCOPUS:0642376850

SN - 0022-3263

VL - 52

SP - 4410

EP - 4412

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr₂, Zn, TiCl₄, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

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