Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

Alison Levens; Adam Ametovski; David Lupton

doi:10.1002/anie.201609330

Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

Alison Levens, Adam Ametovski, David Lupton

School of Chemistry

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

45 Citations (Scopus)

Abstract

Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.

Original language	English
Pages (from-to)	16136-16140
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	52
DOIs	https://doi.org/10.1002/anie.201609330
Publication status	Published - 23 Dec 2016

Keywords

cyclohexanes
donor–acceptor cyclobutanes
enantioselective catalysis
N-heterocyclic carbenes
organocatalysis

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10.1002/anie.201609330

Cite this

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title = "Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis",

abstract = "Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.",

keywords = "cyclohexanes, donor–acceptor cyclobutanes, enantioselective catalysis, N-heterocyclic carbenes, organocatalysis",

author = "Alison Levens and Adam Ametovski and David Lupton",

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T1 - Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

AU - Levens, Alison

AU - Ametovski, Adam

AU - Lupton, David

PY - 2016/12/23

Y1 - 2016/12/23

N2 - Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.

AB - Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.

KW - cyclohexanes

KW - donor–acceptor cyclobutanes

KW - enantioselective catalysis

KW - N-heterocyclic carbenes

KW - organocatalysis

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M3 - Article

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VL - 55

SP - 16136

EP - 16140

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

Abstract

Keywords

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Other files and links

New Reaction Cascades Exploiting N-Heterocyclic Carbenes.

Extending the frontiers of organocatalysis: New reactions involving nucleophilic carbenes

Cite this

Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

Abstract

Keywords

Access to Document

Other files and links

Projects

New Reaction Cascades Exploiting N-Heterocyclic Carbenes.

Extending the frontiers of organocatalysis: New reactions involving nucleophilic carbenes

Cite this