Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions

Felix Kopp; Genia Sklute; Kurt Polborn; Ilan Marek; Paul Knochel

doi:10.1021/ol051452p

Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions

Felix Kopp
, Genia Sklute
, Kurt Polborn
, Ilan Marek
, Paul Knochel

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

32 Scopus citations

Abstract

(Chemical Equation Presented) The reaction of 2,2-dibromo-1-methyl- cyclopropanecarbonitrile (1) with i-PrMgCl in Et₂O/CH ₂Cl₂ provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.

Original language	English (US)
Pages (from-to)	3789-3791
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	17
DOIs	https://doi.org/10.1021/ol051452p
State	Published - Aug 18 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051452p

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title = "Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions",

abstract = "(Chemical Equation Presented) The reaction of 2,2-dibromo-1-methyl- cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH 2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.",

author = "Felix Kopp and Genia Sklute and Kurt Polborn and Ilan Marek and Paul Knochel",

year = "2005",

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doi = "10.1021/ol051452p",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions

AU - Kopp, Felix

AU - Sklute, Genia

AU - Polborn, Kurt

AU - Marek, Ilan

AU - Knochel, Paul

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) The reaction of 2,2-dibromo-1-methyl- cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH 2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.

AB - (Chemical Equation Presented) The reaction of 2,2-dibromo-1-methyl- cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH 2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.

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UR - https://www.scopus.com/pages/publications/24044527853#tab=citedBy

U2 - 10.1021/ol051452p

DO - 10.1021/ol051452p

M3 - Article

C2 - 16092876

AN - SCOPUS:24044527853

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JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions

Abstract

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