Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride

Claire L. Jarvis; Jennifer S. Hirschi; Mathew J. Vetticatt; Daniel Seidel

doi:10.1002/anie.201612148

Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride

Claire L. Jarvis
, Jennifer S. Hirschi
, Mathew J. Vetticatt
, Daniel Seidel

Chemistry

Binghamton University

Rutgers - The State University of New Jersey, New Brunswick

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

60 Scopus citations

Abstract

An amide-thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N-aryl and N-alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio- and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.

Original language	English
Pages (from-to)	2670-2674
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	10
DOIs	https://doi.org/10.1002/anie.201612148
State	Published - Mar 1 2017

Keywords

anion binding
asymmetric catalysis
hydrogen bonding
ion pairing
organocatalysis

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10.1002/anie.201612148

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title = "Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride",

abstract = "An amide-thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N-aryl and N-alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio- and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.",

keywords = "anion binding, asymmetric catalysis, hydrogen bonding, ion pairing, organocatalysis",

author = "Jarvis, \{Claire L.\} and Hirschi, \{Jennifer S.\} and Vetticatt, \{Mathew J.\} and Daniel Seidel",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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T1 - Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride

AU - Jarvis, Claire L.

AU - Hirschi, Jennifer S.

AU - Vetticatt, Mathew J.

AU - Seidel, Daniel

PY - 2017/3/1

Y1 - 2017/3/1

N2 - An amide-thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N-aryl and N-alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio- and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.

AB - An amide-thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N-aryl and N-alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio- and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.

KW - anion binding

KW - asymmetric catalysis

KW - hydrogen bonding

KW - ion pairing

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85011320841

U2 - 10.1002/anie.201612148

DO - 10.1002/anie.201612148

M3 - Article

C2 - 28128534

SN - 1433-7851

VL - 56

SP - 2670

EP - 2674

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride

Abstract

Keywords

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