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

14 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

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

Keywords

Bond Activation
Cyanoamidation
Diastereoselectivity
Homogeneous catalysis
Palladium

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http://europepmc.org/articles/pmc5553975

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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",

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AU - Dreis, Ashley M.

AU - Otte, Sadie C.

AU - Eastwood, Matthew S.

AU - Alonzi, Elizabeth R.

AU - Brethorst, Jason T.

AU - Douglas, Christopher J.

PY - 2017/1/3

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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

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JF - European Journal of Organic Chemistry

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Diastereoselective Intramolecular Cyanoamidation with Alkenes

Abstract

Bibliographical note

Keywords

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