New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones

Guigen Li; Joe Gao; Han Xun Wei; Mason Enright

doi:10.1021/ol9904040

New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones

Guigen Li, Joe Gao, Han Xun Wei, Mason Enright

Chemistry and Biochemistry

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

86 Scopus citations

Abstract

(equation presented) X = Cl: 92%, ZIE > 99/1 X = Br: 85%, ZIE = 9/1 Highly stereoselective vicinal difuctionalization of α/β-unsaturated ketones for the synthesis of multifunctionalized trisubstituted alkenes is described. The new reaction employs titanium(IV) halides (0.5 equiv) as promoters and inexpensive commercial chemicals as starting materials. The reaction can be performed at room temperature in a convenient vial without the protection of inert gases. Good to excellent yields and high Z/E stereoselectivity have been realized in most cases presented (16 examples).

Original language	English
Pages (from-to)	617-620
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	5
DOIs	https://doi.org/10.1021/ol9904040
State	Published - Mar 9 2000

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title = "New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones",

abstract = "(equation presented) X = Cl: 92%, ZIE > 99/1 X = Br: 85%, ZIE = 9/1 Highly stereoselective vicinal difuctionalization of α/β-unsaturated ketones for the synthesis of multifunctionalized trisubstituted alkenes is described. The new reaction employs titanium(IV) halides (0.5 equiv) as promoters and inexpensive commercial chemicals as starting materials. The reaction can be performed at room temperature in a convenient vial without the protection of inert gases. Good to excellent yields and high Z/E stereoselectivity have been realized in most cases presented (16 examples).",

author = "Guigen Li and Joe Gao and Wei, {Han Xun} and Mason Enright",

year = "2000",

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doi = "10.1021/ol9904040",

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journal = "Organic Letters",

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T1 - New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones

AU - Li, Guigen

AU - Gao, Joe

AU - Wei, Han Xun

AU - Enright, Mason

PY - 2000/3/9

Y1 - 2000/3/9

N2 - (equation presented) X = Cl: 92%, ZIE > 99/1 X = Br: 85%, ZIE = 9/1 Highly stereoselective vicinal difuctionalization of α/β-unsaturated ketones for the synthesis of multifunctionalized trisubstituted alkenes is described. The new reaction employs titanium(IV) halides (0.5 equiv) as promoters and inexpensive commercial chemicals as starting materials. The reaction can be performed at room temperature in a convenient vial without the protection of inert gases. Good to excellent yields and high Z/E stereoselectivity have been realized in most cases presented (16 examples).

AB - (equation presented) X = Cl: 92%, ZIE > 99/1 X = Br: 85%, ZIE = 9/1 Highly stereoselective vicinal difuctionalization of α/β-unsaturated ketones for the synthesis of multifunctionalized trisubstituted alkenes is described. The new reaction employs titanium(IV) halides (0.5 equiv) as promoters and inexpensive commercial chemicals as starting materials. The reaction can be performed at room temperature in a convenient vial without the protection of inert gases. Good to excellent yields and high Z/E stereoselectivity have been realized in most cases presented (16 examples).

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M3 - Article

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 5

ER -

New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones

Abstract

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