Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts

Fuxue Chen; Xiaoming Feng; Bo Qin; Guolin Zhang; Yaozhong Jiang

doi:10.1055/s-2003-37534

Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts

Fuxue Chen, Xiaoming Feng^*, Bo Qin, Guolin Zhang, Yaozhong Jiang

^*Corresponding author for this work

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

36 Citations (Scopus)

Abstract

An efficient protocol for addition of TMSCN to ketones by employing 3 mol% achiral Schiff base-Ti(IV) complex as the Lewis acid and 3 mol% N-oxide as the Lewis base in a manner of double activation was described. Aromatic, aliphatic, cyclic and heterocyclic ketones all gave the racemic O-TMS cyanohydrins in good to excellent yields (up to 99%) under mild conditions.

Original language	English
Pages (from-to)	558-560
Number of pages	3
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2003-37534
Publication status	Published - 2003
Externally published	Yes

Keywords

Cyanohydrins
Double activation catalysis
Ketones
N-oxides
Schiff bases

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10.1055/s-2003-37534

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title = "Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts",

abstract = "An efficient protocol for addition of TMSCN to ketones by employing 3 mol% achiral Schiff base-Ti(IV) complex as the Lewis acid and 3 mol% N-oxide as the Lewis base in a manner of double activation was described. Aromatic, aliphatic, cyclic and heterocyclic ketones all gave the racemic O-TMS cyanohydrins in good to excellent yields (up to 99%) under mild conditions.",

keywords = "Cyanohydrins, Double activation catalysis, Ketones, N-oxides, Schiff bases",

author = "Fuxue Chen and Xiaoming Feng and Bo Qin and Guolin Zhang and Yaozhong Jiang",

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doi = "10.1055/s-2003-37534",

language = "English",

pages = "558--560",

journal = "Synlett",

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T1 - Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts

AU - Chen, Fuxue

AU - Feng, Xiaoming

AU - Qin, Bo

AU - Zhang, Guolin

AU - Jiang, Yaozhong

PY - 2003

Y1 - 2003

N2 - An efficient protocol for addition of TMSCN to ketones by employing 3 mol% achiral Schiff base-Ti(IV) complex as the Lewis acid and 3 mol% N-oxide as the Lewis base in a manner of double activation was described. Aromatic, aliphatic, cyclic and heterocyclic ketones all gave the racemic O-TMS cyanohydrins in good to excellent yields (up to 99%) under mild conditions.

AB - An efficient protocol for addition of TMSCN to ketones by employing 3 mol% achiral Schiff base-Ti(IV) complex as the Lewis acid and 3 mol% N-oxide as the Lewis base in a manner of double activation was described. Aromatic, aliphatic, cyclic and heterocyclic ketones all gave the racemic O-TMS cyanohydrins in good to excellent yields (up to 99%) under mild conditions.

KW - Cyanohydrins

KW - Double activation catalysis

KW - Ketones

KW - N-oxides

KW - Schiff bases

UR - http://www.scopus.com/inward/record.url?scp=0037240111&partnerID=8YFLogxK

U2 - 10.1055/s-2003-37534

DO - 10.1055/s-2003-37534

M3 - Article

AN - SCOPUS:0037240111

SN - 0936-5214

SP - 558

EP - 560

JO - Synlett

JF - Synlett

IS - 4

ER -

Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts

Abstract

Keywords

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