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Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes

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Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes. / Doulcet, Julien; Stephenson, G. Richard.
In: Chemistry - A European Journal, Vol. 21, No. 38, 14.09.2015, p. 13431-13436.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Doulcet, J & Stephenson, GR 2015, 'Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes', Chemistry - A European Journal, vol. 21, no. 38, pp. 13431-13436. https://doi.org/10.1002/chem.201501627

APA

Doulcet, J., & Stephenson, G. R. (2015). Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes. Chemistry - A European Journal, 21(38), 13431-13436. https://doi.org/10.1002/chem.201501627

Vancouver

Doulcet J, Stephenson GR. Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes. Chemistry - A European Journal. 2015 Sept 14;21(38):13431-13436. Epub 2015 Sept 2. doi: 10.1002/chem.201501627

Author

Doulcet, Julien ; Stephenson, G. Richard. / Novel Asymmetric Formylation of Aromatic Compounds : Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 38. pp. 13431-13436.

Bibtex

@article{d9c1c96289a04ecc91e81924433677e3,
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. Why have chiral formamides been overlooked for so long as tools in asymmetric synthesis? Herein new and efficient procedures are described in which enantioselective delivery of the formyl group achieves kinetic resolution and double kinetic resolution of helicenes, a class of chiral fused aromatic structures that are notoriously difficult to prepare in enantiopure form.",
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--13436",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "38",

}

RIS

TY - JOUR

T1 - Novel Asymmetric Formylation of Aromatic Compounds

T2 - 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. Why have chiral formamides been overlooked for so long as tools in asymmetric synthesis? Herein new and efficient procedures are described in which enantioselective delivery of the formyl group achieves kinetic resolution and double kinetic resolution of helicenes, a class of chiral fused aromatic structures that are notoriously difficult to prepare in enantiopure form.

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. Why have chiral formamides been overlooked for so long as tools in asymmetric synthesis? Herein new and efficient procedures are described in which enantioselective delivery of the formyl group achieves kinetic resolution and double kinetic resolution of helicenes, a class of chiral fused aromatic structures that are notoriously difficult to prepare in enantiopure form.

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 - Journal article

AN - SCOPUS:84940894151

VL - 21

SP - 13431

EP - 13436

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 38

ER -