The catalytic asymmetric α-benzylation of aldehydes

Benjamin List; Ilija Čoric̈; Oleksandr O. Grygorenko; Philip S.J. Kaib; Igor Komarov; Anna Lee; Markus Leutzsch; Subhas Chandra Pan; Andrey V. Tymtsunik; Manuel Van Gemmeren

doi:10.1002/anie.201306037

The catalytic asymmetric α-benzylation of aldehydes

Benjamin List^*
, Ilija Čoric̈
, Oleksandr O. Grygorenko
, Philip S.J. Kaib
, Igor Komarov
, Anna Lee
, Markus Leutzsch
, Subhas Chandra Pan
, Andrey V. Tymtsunik
, Manuel Van Gemmeren

^*Corresponding author for this work

Department of Chemistry

Max Planck Institute for Coal Research
Kyiv National Taras Shevchenko University

Research output: Contribution to journal › Journal article › peer-review

78 Scopus citations

Abstract

The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.

Original language	English
Pages (from-to)	282-285
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	1
DOIs	https://doi.org/10.1002/anie.201306037
State	Published - 2014.01.3

Keywords

DYKATt
enamine catalysis
organocatalysis
α-alkylation
α-branched aldehydes

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10.1002/anie.201306037

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title = "The catalytic asymmetric α-benzylation of aldehydes",

abstract = "The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.",

keywords = "DYKATt, enamine catalysis, organocatalysis, α-alkylation, α-branched aldehydes",

author = "Benjamin List and Ilija {\v C}ori{\"c} and Grygorenko, \{Oleksandr O.\} and Kaib, \{Philip S.J.\} and Igor Komarov and Anna Lee and Markus Leutzsch and \{Chandra Pan\}, Subhas and Tymtsunik, \{Andrey V.\} and \{Van Gemmeren\}, Manuel",

year = "2014",

month = jan,

day = "3",

doi = "10.1002/anie.201306037",

language = "English",

volume = "53",

pages = "282--285",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - The catalytic asymmetric α-benzylation of aldehydes

AU - List, Benjamin

AU - Čoric̈, Ilija

AU - Grygorenko, Oleksandr O.

AU - Kaib, Philip S.J.

AU - Komarov, Igor

AU - Lee, Anna

AU - Leutzsch, Markus

AU - Chandra Pan, Subhas

AU - Tymtsunik, Andrey V.

AU - Van Gemmeren, Manuel

PY - 2014/1/3

Y1 - 2014/1/3

N2 - The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.

AB - The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities. A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.

KW - DYKATt

KW - enamine catalysis

KW - organocatalysis

KW - α-alkylation

KW - α-branched aldehydes

UR - https://www.scopus.com/pages/publications/84890926781

U2 - 10.1002/anie.201306037

DO - 10.1002/anie.201306037

M3 - Journal article

AN - SCOPUS:84890926781

SN - 1433-7851

VL - 53

SP - 282

EP - 285

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 1

ER -

The catalytic asymmetric α-benzylation of aldehydes

Abstract

Keywords

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