Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis

Junming Mo; Ruojie Yang; Xingkuan Chen; Bhoopendra Tiwari; Yonggui Robin Chi

doi:10.1021/ol303035r

Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis

Junming Mo, Ruojie Yang, Xingkuan Chen, Bhoopendra Tiwari, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

93 Citations (Scopus)

Abstract

A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.

Original language	English
Pages (from-to)	50-53
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	1
DOIs	https://doi.org/10.1021/ol303035r
Publication status	Published - Jan 4 2013
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol303035r

Cite this

@article{fc9ffa34bd614825911c41ed58088feb,

title = "Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis",

abstract = "A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.",

author = "Junming Mo and Ruojie Yang and Xingkuan Chen and Bhoopendra Tiwari and Chi, {Yonggui Robin}",

year = "2013",

month = jan,

day = "4",

doi = "10.1021/ol303035r",

language = "English",

volume = "15",

pages = "50--53",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis

AU - Mo, Junming

AU - Yang, Ruojie

AU - Chen, Xingkuan

AU - Tiwari, Bhoopendra

AU - Chi, Yonggui Robin

PY - 2013/1/4

Y1 - 2013/1/4

N2 - A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.

AB - A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.

UR - http://www.scopus.com/inward/record.url?scp=84874026771&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874026771&partnerID=8YFLogxK

U2 - 10.1021/ol303035r

DO - 10.1021/ol303035r

M3 - Article

C2 - 23249417

AN - SCOPUS:84874026771

SN - 1523-7060

VL - 15

SP - 50

EP - 53

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Direct α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this