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

Research output: Contribution to journal › Article (Academic Journal) › peer-review

41 Citations (Scopus)

605 Downloads (Pure)

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 Sept 2016
DOIs	https://doi.org/10.1021/jacs.6b07046
Publication status	Published - 14 Sept 2016

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

SN - 0002-7863

VL - 138

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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

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