The productive merger of iodonium salts and organocatalysis: A non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes

Anna E. Allen; David W.C. MacMillan

doi:10.1021/ja100748y

The productive merger of iodonium salts and organocatalysis: A non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes

Anna E. Allen, David W.C. MacMillan

Chemistry

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

275 Scopus citations

Abstract

An enantioselective organocatalytic α-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched α-trifluoromethylated aldehydes through a nonphotolytic pathway.

Original language	English (US)
Pages (from-to)	4986-4987
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	132
Issue number	14
DOIs	https://doi.org/10.1021/ja100748y
State	Published - Apr 14 2010

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja100748y

Fingerprint Dive into the research topics of 'The productive merger of iodonium salts and organocatalysis: A non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes'. Together they form a unique fingerprint.

Cite this

@article{e23b9f11d9cd45ea804d5594ee4292a7,

title = "The productive merger of iodonium salts and organocatalysis: A non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes",

abstract = "An enantioselective organocatalytic α-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched α-trifluoromethylated aldehydes through a nonphotolytic pathway.",

author = "Allen, {Anna E.} and MacMillan, {David W.C.}",

year = "2010",

month = apr,

day = "14",

doi = "10.1021/ja100748y",

language = "English (US)",

volume = "132",

pages = "4986--4987",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - The productive merger of iodonium salts and organocatalysis

T2 - A non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes

AU - Allen, Anna E.

AU - MacMillan, David W.C.

PY - 2010/4/14

Y1 - 2010/4/14

N2 - An enantioselective organocatalytic α-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched α-trifluoromethylated aldehydes through a nonphotolytic pathway.

AB - An enantioselective organocatalytic α-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched α-trifluoromethylated aldehydes through a nonphotolytic pathway.

UR - http://www.scopus.com/inward/record.url?scp=77950854848&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77950854848&partnerID=8YFLogxK

U2 - 10.1021/ja100748y

DO - 10.1021/ja100748y

M3 - Article

C2 - 20297822

AN - SCOPUS:77950854848

VL - 132

SP - 4986

EP - 4987

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 14

ER -