Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters

Richard Frantz; Lukas Hintermann; Mauro Perseghini; Diego Broggini; Antonio Togni

doi:10.1021/ol0343459

Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters

Richard Frantz, Lukas Hintermann, Mauro Perseghini, Diego Broggini, Antonio Togni

ETH Zurich

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

122 Scopus citations

Abstract

(Matrix presented) β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl₃ as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl₂(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.

Original language	English
Pages (from-to)	1709-1712
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	10
DOIs	https://doi.org/10.1021/ol0343459
State	Published - 15 May 2003
Externally published	Yes

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title = "Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters",

abstract = "(Matrix presented) β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl3 as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl2(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.",

author = "Richard Frantz and Lukas Hintermann and Mauro Perseghini and Diego Broggini and Antonio Togni",

year = "2003",

month = may,

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doi = "10.1021/ol0343459",

language = "English",

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pages = "1709--1712",

journal = "Organic Letters",

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T1 - Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters

AU - Frantz, Richard

AU - Hintermann, Lukas

AU - Perseghini, Mauro

AU - Broggini, Diego

AU - Togni, Antonio

PY - 2003/5/15

Y1 - 2003/5/15

N2 - (Matrix presented) β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl3 as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl2(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.

AB - (Matrix presented) β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl3 as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl2(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.

UR - http://www.scopus.com/inward/record.url?scp=0141518173&partnerID=8YFLogxK

U2 - 10.1021/ol0343459

DO - 10.1021/ol0343459

M3 - Article

AN - SCOPUS:0141518173

SN - 1523-7060

VL - 5

SP - 1709

EP - 1712

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters

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