An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

Jason A. Miller; Wiechang Jin; Sonbinh T. Nguyen

doi:10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2

An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

Jason A. Miller, Wiechang Jin, Sonbinh T. Nguyen^*

^*Corresponding author for this work

Chemistry

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

113 Scopus citations

Abstract

Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).

Original language	English (US)
Pages (from-to)	2953-2956
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	16
DOIs	https://doi.org/10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2
State	Published - Aug 16 2002

Keywords

Asymmetric catalysis
Cyclopropanation
N,O ligands
Ruthenium

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2

Cite this

@article{3815194dbe424aa2b0bc8097950d69d3,

title = "An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes",

abstract = "Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).",

keywords = "Asymmetric catalysis, Cyclopropanation, N,O ligands, Ruthenium",

author = "Miller, {Jason A.} and Wiechang Jin and Nguyen, {Sonbinh T.}",

year = "2002",

month = aug,

day = "16",

doi = "10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2",

language = "English (US)",

volume = "41",

pages = "2953--2956",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "16",

}

TY - JOUR

T1 - An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

AU - Miller, Jason A.

AU - Jin, Wiechang

AU - Nguyen, Sonbinh T.

PY - 2002/8/16

Y1 - 2002/8/16

N2 - Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).

AB - Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).

KW - Asymmetric catalysis

KW - Cyclopropanation

KW - N,O ligands

KW - Ruthenium

UR - http://www.scopus.com/inward/record.url?scp=0037119302&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037119302&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2

DO - 10.1002/1521-3773(20020816)41:16<2953::AID-ANIE2953>3.0.CO;2-2

M3 - Article

C2 - 12203422

AN - SCOPUS:0037119302

SN - 1433-7851

VL - 41

SP - 2953

EP - 2956

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 16

ER -

An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this