Capture–Collapse Heterocyclization: 1,3-Diazepanes by C–N Reductive Elimination from Rhodacyclopentanones

Niall McCreanor; Steven Stanton; John Bower

doi:10.1021/jacs.6b07046

Capture–Collapse Heterocyclization: 1,3-Diazepanes by C–N Reductive Elimination from Rhodacyclopentanones

Niall McCreanor, Steven Stanton, John Bower

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Abstract

Rhodacyclopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be “captured” by pendant nucleophiles prior to “collapse” to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively. The results outlined here validate a potentially general approach to medium-ring heterocycles

Original language	English
Pages (from-to)	11465-11468
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	36
Early online date	2 Sep 2016
DOIs	https://doi.org/10.1021/jacs.6b07046
Publication status	Published - 14 Sep 2016

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BCS and TECS CDTs

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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P.
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Capture–Collapse Heterocyclization: 1,3-Diazepanes by C–N Reductive Elimination from Rhodacyclopentanones",

abstract = "Rhodacyclopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be “captured” by pendant nucleophiles prior to “collapse” to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively. The results outlined here validate a potentially general approach to medium-ring heterocycles",

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journal = "Journal of the American Chemical Society",

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AU - McCreanor, Niall

AU - Stanton, Steven

AU - Bower, John

PY - 2016/9/14

Y1 - 2016/9/14

N2 - Rhodacyclopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be “captured” by pendant nucleophiles prior to “collapse” to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively. The results outlined here validate a potentially general approach to medium-ring heterocycles

AB - Rhodacyclopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be “captured” by pendant nucleophiles prior to “collapse” to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively. The results outlined here validate a potentially general approach to medium-ring heterocycles

U2 - 10.1021/jacs.6b07046

DO - 10.1021/jacs.6b07046

M3 - Article (Academic Journal)

C2 - 27589060

VL - 138

SP - 11465

EP - 11468

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 36

ER -

Capture–Collapse Heterocyclization: 1,3-Diazepanes by C–N Reductive Elimination from Rhodacyclopentanones

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Cite this