Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst

Xiao Han; Jacek Kwiatkowski; Teng Xue; Kuo Wei Huang; Yixin Lu

doi:10.1002/anie.200903635

Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst

Xiao Han^*, Jacek Kwiatkowski, Teng Xue, Kuo Wei Huang, Yixin Lu

^*Corresponding author for this work

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

175 Scopus citations

Abstract

Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

Original language	English (US)
Pages (from-to)	7604-7607
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	41
DOIs	https://doi.org/10.1002/anie.200903635
State	Published - Sep 28 2009
Externally published	Yes

Keywords

Asymmetric synthesis
Fluorination
Mannich reaction
Organocatalysis
Quaternary stereocenters

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200903635

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abstract = "Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).",

keywords = "Asymmetric synthesis, Fluorination, Mannich reaction, Organocatalysis, Quaternary stereocenters",

author = "Xiao Han and Jacek Kwiatkowski and Teng Xue and Huang, {Kuo Wei} and Yixin Lu",

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AU - Han, Xiao

AU - Kwiatkowski, Jacek

AU - Xue, Teng

AU - Huang, Kuo Wei

AU - Lu, Yixin

PY - 2009/9/28

Y1 - 2009/9/28

N2 - Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

AB - Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

KW - Asymmetric synthesis

KW - Fluorination

KW - Mannich reaction

KW - Organocatalysis

KW - Quaternary stereocenters

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U2 - 10.1002/anie.200903635

DO - 10.1002/anie.200903635

M3 - Article

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AN - SCOPUS:70349995077

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EP - 7607

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 41

ER -

Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst

Abstract

Keywords

ASJC Scopus subject areas

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