Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones

Catherine N. Slattery; Leslie Ann Clarke; Alan Ford; Anita R. Maguire

doi:10.1016/j.tet.2012.12.003

Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones

Catherine N. Slattery
, Leslie Ann Clarke
, Alan Ford
, Anita R. Maguire

University College Cork

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

Abstract

Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazosulfones in the presence of various group I salts are reported leading to substantial variation in reaction efficiencies and enantioselectivities. The borate additives NaBARF and KBARF were found to be the most effective additives for permitting highly enantioselective syntheses with short reactions times and high efficiency. Significantly, direct evidence of the critical role of the additive in enantioselective carbenoid reactions has been secured.

Original language	English
Pages (from-to)	1297-1301
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2012.12.003
Publication status	Published - 28 Jan 2013

Keywords

Bis(oxazoline)
C-H insertion
Copper catalysis
Diazo
NaBARF

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title = "Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones",

abstract = "Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazosulfones in the presence of various group I salts are reported leading to substantial variation in reaction efficiencies and enantioselectivities. The borate additives NaBARF and KBARF were found to be the most effective additives for permitting highly enantioselective syntheses with short reactions times and high efficiency. Significantly, direct evidence of the critical role of the additive in enantioselective carbenoid reactions has been secured.",

keywords = "Bis(oxazoline), C-H insertion, Copper catalysis, Diazo, NaBARF",

author = "Slattery, \{Catherine N.\} and Clarke, \{Leslie Ann\} and Alan Ford and Maguire, \{Anita R.\}",

year = "2013",

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doi = "10.1016/j.tet.2012.12.003",

language = "English",

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journal = "Tetrahedron",

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T1 - Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones

AU - Slattery, Catherine N.

AU - Clarke, Leslie Ann

AU - Ford, Alan

AU - Maguire, Anita R.

PY - 2013/1/28

Y1 - 2013/1/28

N2 - Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazosulfones in the presence of various group I salts are reported leading to substantial variation in reaction efficiencies and enantioselectivities. The borate additives NaBARF and KBARF were found to be the most effective additives for permitting highly enantioselective syntheses with short reactions times and high efficiency. Significantly, direct evidence of the critical role of the additive in enantioselective carbenoid reactions has been secured.

AB - Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazosulfones in the presence of various group I salts are reported leading to substantial variation in reaction efficiencies and enantioselectivities. The borate additives NaBARF and KBARF were found to be the most effective additives for permitting highly enantioselective syntheses with short reactions times and high efficiency. Significantly, direct evidence of the critical role of the additive in enantioselective carbenoid reactions has been secured.

KW - Bis(oxazoline)

KW - C-H insertion

KW - Copper catalysis

KW - Diazo

KW - NaBARF

UR - https://www.scopus.com/pages/publications/84871995017

U2 - 10.1016/j.tet.2012.12.003

DO - 10.1016/j.tet.2012.12.003

M3 - Article

AN - SCOPUS:84871995017

SN - 0040-4020

VL - 69

SP - 1297

EP - 1301

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones

Abstract

Keywords

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