Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

Julien Doulcet; G. Richard Stephenson

doi:10.1002/chem.201501627

Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

Julien Doulcet
, G. Richard Stephenson

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

21 Citations (Scopus)

23 Downloads (Pure)

Abstract

Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this
study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.

Original language	English
Pages (from-to)	13431–13436
Number of pages	6
Journal	Chemistry - A European Journal
Volume	21
Issue number	38
Early online date	4 Aug 2015
DOIs	https://doi.org/10.1002/chem.201501627
Publication status	Published - 14 Sept 2015

Keywords

asymmetric synthesis
chiral formamides
double kinetic resolution
enantioselective formylation
kinetic resolution

Access to Document

10.1002/chem.201501627

Stepehnson-Doulcet_DOI_10.1002_chem.201501627Accepted author manuscript, 1.59 MB

G.Richard Stephenson
- G.R.Stephensonuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Emeritus Professor
Person: Honorary

2 Finished

A-I CHEM CHANNEL (INTERREG)
Stephenson, G. R. (Principal Investigator), Arnaux, V. (Co-Investigator), Bew, S. (Co-Investigator), Bulman Page, P. (Co-Investigator), Cammidge, A. (Co-Investigator), David, F.-X. (Co-Investigator), Franck, X. (Co-Investigator), Harrowven, D. (Co-Investigator), Homme, A. (Co-Investigator), Mulot, I. (Co-Investigator), Munoz-Herranz, M. P. (Co-Investigator), Richards, C. (Co-Investigator), Rouden, J. (Co-Investigator), Yves, R. (Co-Investigator), Chan, Y. (Researcher) & Fernandes, I. (Researcher)
European Regional Development Fund
2/11/11 → 30/06/15
Project: Research
Highly anisotropic helicene - based NLOphores for 2 photon circular dichroism
Stephenson, G. R. (Principal Investigator)
Engineering and Physical Sciences Research Council
1/10/09 → 30/09/13
Project: Research

21 Citations
1 Article

The use of (–)-sparteine/organolithium reagents for the enantioselective lithiation of 7,8-dipropyltetrathia[7]helicene: single and double kinetic resolution procedures
Doulcet, J. & Stephenson, G. R., 14 Dec 2015, In: Chemistry - A European Journal. 21, 51, p. 18677-18689 13 p.
Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Cite this

@article{acf9611bfb244c42aa68d749df3903e6,

title = "Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes",

abstract = "Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73\% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.",

keywords = "asymmetric synthesis, chiral formamides, double kinetic resolution, enantioselective formylation, kinetic resolution",

author = "Julien Doulcet and Stephenson, \{G. Richard\}",

year = "2015",

month = sep,

day = "14",

doi = "10.1002/chem.201501627",

language = "English",

volume = "21",

pages = "13431{\textendash}13436",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley",

number = "38",

}

TY - JOUR

T1 - Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

AU - Doulcet, Julien

AU - Stephenson, G. Richard

PY - 2015/9/14

Y1 - 2015/9/14

N2 - Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.

AB - Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.

KW - asymmetric synthesis

KW - chiral formamides

KW - double kinetic resolution

KW - enantioselective formylation

KW - kinetic resolution

U2 - 10.1002/chem.201501627

DO - 10.1002/chem.201501627

M3 - Article

SN - 0947-6539

VL - 21

SP - 13431

EP - 13436

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 38

ER -

Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

Abstract

Keywords

Access to Document

Profiles

G.Richard Stephenson

Projects

A-I CHEM CHANNEL (INTERREG)

Highly anisotropic helicene - based NLOphores for 2 photon circular dichroism

Research output

The use of (–)-sparteine/organolithium reagents for the enantioselective lithiation of 7,8-dipropyltetrathia[7]helicene: single and double kinetic resolution procedures

Cite this