Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents

Zhi Liang Shen; Zhihua Peng; Chun Ming Yang; Julian Helberg; Peter Mayer; Ilan Marek; Paul Knochel

doi:10.1021/ol403692k

Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents

Zhi Liang Shen, Zhihua Peng, Chun Ming Yang, Julian Helberg, Peter Mayer, Ilan Marek, Paul Knochel

Technion - Israel Institute of Technology

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

Abstract

Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.

Original language	English
Pages (from-to)	956-959
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	3
DOIs	https://doi.org/10.1021/ol403692k
State	Published - 7 Feb 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol403692k

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title = "Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents",

abstract = "Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.",

author = "Shen, {Zhi Liang} and Zhihua Peng and Yang, {Chun Ming} and Julian Helberg and Peter Mayer and Ilan Marek and Paul Knochel",

year = "2014",

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doi = "10.1021/ol403692k",

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journal = "Organic Letters",

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AU - Shen, Zhi Liang

AU - Peng, Zhihua

AU - Yang, Chun Ming

AU - Helberg, Julian

AU - Mayer, Peter

AU - Marek, Ilan

AU - Knochel, Paul

PY - 2014/2/7

Y1 - 2014/2/7

N2 - Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.

AB - Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.

UR - http://www.scopus.com/inward/record.url?scp=84893820118&partnerID=8YFLogxK

U2 - 10.1021/ol403692k

DO - 10.1021/ol403692k

M3 - مقالة

SN - 1523-7060

VL - 16

SP - 956

EP - 959

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents

Abstract

All Science Journal Classification (ASJC) codes

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