Diastereoselective Intramolecular Cyanoamidation with Alkenes

Ashley M. Dreis; Sadie C. Otte; Matthew S. Eastwood; Elizabeth R. Alonzi; Jason T. Brethorst; Christopher J. Douglas

doi:10.1002/ejoc.201601283

Diastereoselective Intramolecular Cyanoamidation with Alkenes

Ashley M. Dreis, Sadie C. Otte, Matthew S. Eastwood, Elizabeth R. Alonzi, Jason T. Brethorst, Christopher J. Douglas

Chemistry (Twin Cities)

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

12 Scopus citations

Abstract

Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.

Original language	English (US)
Pages (from-to)	45-48
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201601283
State	Published - Jan 3 2017

Bibliographical note

Funding Information:
This work was funded by the National Institute of Health (R01 GM095559). NMR spectra were recorded on an instrument purchased with support from the National Institute of Health (S10 OD011952). E. R. A. thanks the University of Minnesota for support through the Undergraduate Research Opportunities Program (UROP) award. We also thank Dr. Letitia Yao (UMN) for NMR assistance and Zhongda Pan (UMN) for constructive conversations and purification of chemical reagents.

Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Bond Activation
Cyanoamidation
Diastereoselectivity
Homogeneous catalysis
Palladium

Publisher link

10.1002/ejoc.201601283

http://europepmc.org/articles/pmc5553975

Find It

Find It at U of M Libraries

Cite this

@article{2acd59a8024e44cdb2ab3333442cd6fb,

title = "Diastereoselective Intramolecular Cyanoamidation with Alkenes",

abstract = "Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.",

keywords = "Bond Activation, Cyanoamidation, Diastereoselectivity, Homogeneous catalysis, Palladium",

author = "Dreis, {Ashley M.} and Otte, {Sadie C.} and Eastwood, {Matthew S.} and Alonzi, {Elizabeth R.} and Brethorst, {Jason T.} and Douglas, {Christopher J.}",

note = "Funding Information: This work was funded by the National Institute of Health (R01 GM095559). NMR spectra were recorded on an instrument purchased with support from the National Institute of Health (S10 OD011952). E. R. A. thanks the University of Minnesota for support through the Undergraduate Research Opportunities Program (UROP) award. We also thank Dr. Letitia Yao (UMN) for NMR assistance and Zhongda Pan (UMN) for constructive conversations and purification of chemical reagents. Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = jan,

day = "3",

doi = "10.1002/ejoc.201601283",

language = "English (US)",

volume = "2017",

pages = "45--48",

journal = "Justus Liebigs Annalen der Chemie",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "1",

}

TY - JOUR

T1 - Diastereoselective Intramolecular Cyanoamidation with Alkenes

AU - Dreis, Ashley M.

AU - Otte, Sadie C.

AU - Eastwood, Matthew S.

AU - Alonzi, Elizabeth R.

AU - Brethorst, Jason T.

AU - Douglas, Christopher J.

N1 - Funding Information: This work was funded by the National Institute of Health (R01 GM095559). NMR spectra were recorded on an instrument purchased with support from the National Institute of Health (S10 OD011952). E. R. A. thanks the University of Minnesota for support through the Undergraduate Research Opportunities Program (UROP) award. We also thank Dr. Letitia Yao (UMN) for NMR assistance and Zhongda Pan (UMN) for constructive conversations and purification of chemical reagents. Publisher Copyright: © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/1/3

Y1 - 2017/1/3

N2 - Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.

AB - Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.

KW - Bond Activation

KW - Cyanoamidation

KW - Diastereoselectivity

KW - Homogeneous catalysis

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=85006698905&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85006698905&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201601283

DO - 10.1002/ejoc.201601283

M3 - Article

C2 - 28808413

AN - SCOPUS:85006698905

SN - 1434-193X

VL - 2017

SP - 45

EP - 48

JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

IS - 1

ER -

Diastereoselective Intramolecular Cyanoamidation with Alkenes

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this