α-Substituent effect on olefination of ester carbonyl groups with ynolates

Satoshi Umezu; Mitsuru Shindo

doi:10.1016/j.tetlet.2013.10.027

α-Substituent effect on olefination of ester carbonyl groups with ynolates

Satoshi Umezu, Mitsuru Shindo

Department of Fundamental Organic Chemistry

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

5 Citations (Scopus)

Abstract

In the olefination reaction of ester carbonyl with ynolate, an α-hetero (N, O, S)-substituent on the substrates was found to markedly improve the yields of tetrasubstituted olefins, even though it was sterically hindered. The α-substituent effect may be due to several factors including the addition based on the polar Felkin–Anh model and restricted conformation of the initial adducts.

Original language	English
Pages (from-to)	6871-6873
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.027
Publication status	Published - Dec 11 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.10.027

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title = "α-Substituent effect on olefination of ester carbonyl groups with ynolates",

abstract = "In the olefination reaction of ester carbonyl with ynolate, an α-hetero (N, O, S)-substituent on the substrates was found to markedly improve the yields of tetrasubstituted olefins, even though it was sterically hindered. The α-substituent effect may be due to several factors including the addition based on the polar Felkin–Anh model and restricted conformation of the initial adducts.",

author = "Satoshi Umezu and Mitsuru Shindo",

note = "Funding Information: This work was supported by the Program for the Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN) from the Bio-oriented Technology Research Advancement Institution, and JSPS KAKENHI Grant Number 24106731 , 22390002 . ",

year = "2013",

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doi = "10.1016/j.tetlet.2013.10.027",

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journal = "Tetrahedron Letters",

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T1 - α-Substituent effect on olefination of ester carbonyl groups with ynolates

AU - Umezu, Satoshi

AU - Shindo, Mitsuru

N1 - Funding Information: This work was supported by the Program for the Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN) from the Bio-oriented Technology Research Advancement Institution, and JSPS KAKENHI Grant Number 24106731 , 22390002 .

PY - 2013/12/11

Y1 - 2013/12/11

N2 - In the olefination reaction of ester carbonyl with ynolate, an α-hetero (N, O, S)-substituent on the substrates was found to markedly improve the yields of tetrasubstituted olefins, even though it was sterically hindered. The α-substituent effect may be due to several factors including the addition based on the polar Felkin–Anh model and restricted conformation of the initial adducts.

AB - In the olefination reaction of ester carbonyl with ynolate, an α-hetero (N, O, S)-substituent on the substrates was found to markedly improve the yields of tetrasubstituted olefins, even though it was sterically hindered. The α-substituent effect may be due to several factors including the addition based on the polar Felkin–Anh model and restricted conformation of the initial adducts.

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DO - 10.1016/j.tetlet.2013.10.027

M3 - Article

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SN - 0040-4039

VL - 54

SP - 6871

EP - 6873

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

α-Substituent effect on olefination of ester carbonyl groups with ynolates

Abstract

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