Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones.

Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Research Abstract Details 

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Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Abstract Text:

High-yielding cyanosilylation of ketones with NaCN and various chlorotrialkylsilanes in DMSO proceeds smoothly without catalysis to give silyl-protected ketone cyanohydrins. The unique role of DMSO consists in rendering naked cyanide anions that reversibly add to the C double bond O bond at the rate-determining step followed by fast trapping of the transient tertiary sodium cyanoalcoholates with chlorotrialkylsilanes or in situ generated cyanotrialkylsilanes. Preparatively, the reaction matches the best known catalytic cyanosilylation systems applying expensive Me(3)SiCN and demonstrates unprecedented efficiency in the synthesis of sterically congested trialkylsilyl-protected cyanohydrins.

Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Publishing Authors By Initials

For similar inorganic chemicals: silicon compounds: silanes research abstracts see: inorganic chemicals: silicon compounds: silanes research

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Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: The Journal of organic chemistry

VOLUME: 73

Page Numbers: 2446-9

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 29

MONTH: 02

YEAR: 2008

Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Keywords Mesh Terms:

KEYWORDS: Silanes

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones. Information

Substance Name: cyanohydrin

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Grant and Affiliation Information for Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones.

AFFILIATION: Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, S(627833), Singapore.

Country: United States

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MEDLINETA: J Org Chem

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