Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

Yi Wang; Hon Wai Lam

doi:10.1021/jo802475x

Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

Yi Wang, Hon Wai Lam

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

Abstract

In the presence of stoichiometric magnesium halides, a range of bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multi substituted alkenyl halides. More highly functionalized compounds may be obtained by trapping of the magnesium enolate intermediates in situ.

Original language	English
Pages (from-to)	1353-1355
Number of pages	3
Journal	The Journal of Organic Chemistry (JOC)
Volume	74
Issue number	3
DOIs	https://doi.org/10.1021/jo802475x
Publication status	Published - 6 Feb 2009

Keywords / Materials (for Non-textual outputs)

NUCLEOPHILIC VINYLIC SUBSTITUTIONS
S(N)2 SUBSTITUTION
CARBON
INVERSION
CONFIGURATION
CARBOMETALATION
DERIVATIVES
CHEMISTRY
ADDITIONS
REAGENTS

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10.1021/jo802475x

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title = "Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes",

abstract = "In the presence of stoichiometric magnesium halides, a range of bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multi substituted alkenyl halides. More highly functionalized compounds may be obtained by trapping of the magnesium enolate intermediates in situ.",

keywords = "NUCLEOPHILIC VINYLIC SUBSTITUTIONS, S(N)2 SUBSTITUTION, CARBON, INVERSION, CONFIGURATION, CARBOMETALATION, DERIVATIVES, CHEMISTRY, ADDITIONS, REAGENTS",

author = "Yi Wang and Lam, {Hon Wai}",

year = "2009",

month = feb,

day = "6",

doi = "10.1021/jo802475x",

language = "English",

volume = "74",

pages = "1353--1355",

journal = "The Journal of Organic Chemistry (JOC)",

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T1 - Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

AU - Wang, Yi

AU - Lam, Hon Wai

PY - 2009/2/6

Y1 - 2009/2/6

N2 - In the presence of stoichiometric magnesium halides, a range of bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multi substituted alkenyl halides. More highly functionalized compounds may be obtained by trapping of the magnesium enolate intermediates in situ.

AB - In the presence of stoichiometric magnesium halides, a range of bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multi substituted alkenyl halides. More highly functionalized compounds may be obtained by trapping of the magnesium enolate intermediates in situ.

KW - NUCLEOPHILIC VINYLIC SUBSTITUTIONS

KW - S(N)2 SUBSTITUTION

KW - CARBON

KW - INVERSION

KW - CONFIGURATION

KW - CARBOMETALATION

KW - DERIVATIVES

KW - CHEMISTRY

KW - ADDITIONS

KW - REAGENTS

UR - http://www.scopus.com/inward/record.url?scp=64549124388&partnerID=8YFLogxK

U2 - 10.1021/jo802475x

DO - 10.1021/jo802475x

M3 - Article

SN - 1520-6904

VL - 74

SP - 1353

EP - 1355

JO - The Journal of Organic Chemistry (JOC)

JF - The Journal of Organic Chemistry (JOC)

IS - 3

ER -

Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

Abstract

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