Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts

Magnus Rueping; Erli Sugiono; Stefan A. Moreth

doi:10.1002/adsc.200600405

Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts

Magnus Rueping^*, Erli Sugiono, Stefan A. Moreth

^*Corresponding author for this work

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

126 Scopus citations

Abstract

An efficient, metal-free Brønsted acid-catalyzed, enantioselective hydrocyanation of ketoimines has been developed. This BINOL phosphate-catalyzed Strecker reaction provides the corresponding amino nitriles, precursors of quaternary amino acids, in good isolated yields and enantioselectivities. Additionally, we demonstrate that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.

Original language	English (US)
Pages (from-to)	759-764
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	4-5
DOIs	https://doi.org/10.1002/adsc.200600405
State	Published - Mar 2007
Externally published	Yes

Keywords

Amino acids
BINOL phosphate
Brønsted acid
Hydrocyanation
Strecker reaction
TADDOL

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200600405

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title = "Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts",

abstract = "An efficient, metal-free Br{\o}nsted acid-catalyzed, enantioselective hydrocyanation of ketoimines has been developed. This BINOL phosphate-catalyzed Strecker reaction provides the corresponding amino nitriles, precursors of quaternary amino acids, in good isolated yields and enantioselectivities. Additionally, we demonstrate that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.",

keywords = "Amino acids, BINOL phosphate, Br{\o}nsted acid, Hydrocyanation, Strecker reaction, TADDOL",

author = "Magnus Rueping and Erli Sugiono and Moreth, {Stefan A.}",

year = "2007",

month = mar,

doi = "10.1002/adsc.200600405",

language = "English (US)",

volume = "349",

pages = "759--764",

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issn = "1615-4150",

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T1 - Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts

AU - Rueping, Magnus

AU - Sugiono, Erli

AU - Moreth, Stefan A.

PY - 2007/3

Y1 - 2007/3

N2 - An efficient, metal-free Brønsted acid-catalyzed, enantioselective hydrocyanation of ketoimines has been developed. This BINOL phosphate-catalyzed Strecker reaction provides the corresponding amino nitriles, precursors of quaternary amino acids, in good isolated yields and enantioselectivities. Additionally, we demonstrate that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.

AB - An efficient, metal-free Brønsted acid-catalyzed, enantioselective hydrocyanation of ketoimines has been developed. This BINOL phosphate-catalyzed Strecker reaction provides the corresponding amino nitriles, precursors of quaternary amino acids, in good isolated yields and enantioselectivities. Additionally, we demonstrate that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.

KW - Amino acids

KW - BINOL phosphate

KW - Brønsted acid

KW - Hydrocyanation

KW - Strecker reaction

KW - TADDOL

UR - http://www.scopus.com/inward/record.url?scp=34250780205&partnerID=8YFLogxK

U2 - 10.1002/adsc.200600405

DO - 10.1002/adsc.200600405

M3 - Article

AN - SCOPUS:34250780205

SN - 1615-4150

VL - 349

SP - 759

EP - 764

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 4-5

ER -

Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts

Abstract

Keywords

ASJC Scopus subject areas

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