Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones

Anita E. Mattson; Karl A Scheidt

Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones

Anita E. Mattson, Karl A Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article

87 Scopus citations

Abstract

(Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.

Original language	English (US)
Pages (from-to)	4363-4366
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	23
State	Published - Nov 11 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones",

abstract = "(Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.",

author = "Mattson, {Anita E.} and Scheidt, {Karl A}",

year = "2004",

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language = "English (US)",

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AU - Scheidt, Karl A

PY - 2004/11/11

Y1 - 2004/11/11

N2 - (Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.

AB - (Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.

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VL - 6

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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