Diastereoselective synthesis of planar chiral cobalt metallocene based oxazoline platinacycles

M. E. Gunay; David Hughes; C. J. Richards

doi:10.1021/om200353n

Diastereoselective synthesis of planar chiral cobalt metallocene based oxazoline platinacycles

M. E. Gunay, David Hughes, C. J. Richards

Chemistry of Materials and Catalysis

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

10 Citations (Scopus)

Abstract

Reaction of (eta(5)-(S)-2-(4-methylethyl)oxazolinyl-cyclopentadienyl)(eta(4)-tetraph enylcyclobutadiene)cobalt with cis-bis(dimethylsulfoxide)dichloroplatinum gave a 4.7:1 ratio of diastereomeric platinacycles, and the S,R(p)-configuration of the major isomer was determined by X-ray crystallography. The same reaction on the corresponding t-Bu-substituted oxazoline derivative proceeded with a 5.6:1 selectivity, with the S,R(p)-configuration of the major isomer determined by circular dichroism. Dimethylsulfoxide- and triphenylphosphine-ligated complexes are inactive as catalysts for the allylic imidate rearrangement of a trichloroacetimidate.

Original language	English
Pages (from-to)	3901-3904
Number of pages	4
Journal	Organometallics
Volume	30
Issue number	14
DOIs	https://doi.org/10.1021/om200353n
Publication status	Published - 2011

Access to Document

10.1021/om200353n

Cite this

@article{7becc57c31d54392a5a77bd5950d1dc5,

title = "Diastereoselective synthesis of planar chiral cobalt metallocene based oxazoline platinacycles",

abstract = "Reaction of (eta(5)-(S)-2-(4-methylethyl)oxazolinyl-cyclopentadienyl)(eta(4)-tetraph enylcyclobutadiene)cobalt with cis-bis(dimethylsulfoxide)dichloroplatinum gave a 4.7:1 ratio of diastereomeric platinacycles, and the S,R(p)-configuration of the major isomer was determined by X-ray crystallography. The same reaction on the corresponding t-Bu-substituted oxazoline derivative proceeded with a 5.6:1 selectivity, with the S,R(p)-configuration of the major isomer determined by circular dichroism. Dimethylsulfoxide- and triphenylphosphine-ligated complexes are inactive as catalysts for the allylic imidate rearrangement of a trichloroacetimidate.",

author = "Gunay, {M. E.} and David Hughes and Richards, {C. J.}",

note = "Guenay, M. Emin Hughes, David L. Richards, Christopher J.",

year = "2011",

doi = "10.1021/om200353n",

language = "English",

volume = "30",

pages = "3901--3904",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Diastereoselective synthesis of planar chiral cobalt metallocene based oxazoline platinacycles

AU - Gunay, M. E.

AU - Hughes, David

AU - Richards, C. J.

N1 - Guenay, M. Emin Hughes, David L. Richards, Christopher J.

PY - 2011

Y1 - 2011

N2 - Reaction of (eta(5)-(S)-2-(4-methylethyl)oxazolinyl-cyclopentadienyl)(eta(4)-tetraph enylcyclobutadiene)cobalt with cis-bis(dimethylsulfoxide)dichloroplatinum gave a 4.7:1 ratio of diastereomeric platinacycles, and the S,R(p)-configuration of the major isomer was determined by X-ray crystallography. The same reaction on the corresponding t-Bu-substituted oxazoline derivative proceeded with a 5.6:1 selectivity, with the S,R(p)-configuration of the major isomer determined by circular dichroism. Dimethylsulfoxide- and triphenylphosphine-ligated complexes are inactive as catalysts for the allylic imidate rearrangement of a trichloroacetimidate.

AB - Reaction of (eta(5)-(S)-2-(4-methylethyl)oxazolinyl-cyclopentadienyl)(eta(4)-tetraph enylcyclobutadiene)cobalt with cis-bis(dimethylsulfoxide)dichloroplatinum gave a 4.7:1 ratio of diastereomeric platinacycles, and the S,R(p)-configuration of the major isomer was determined by X-ray crystallography. The same reaction on the corresponding t-Bu-substituted oxazoline derivative proceeded with a 5.6:1 selectivity, with the S,R(p)-configuration of the major isomer determined by circular dichroism. Dimethylsulfoxide- and triphenylphosphine-ligated complexes are inactive as catalysts for the allylic imidate rearrangement of a trichloroacetimidate.

U2 - 10.1021/om200353n

DO - 10.1021/om200353n

M3 - Article

VL - 30

SP - 3901

EP - 3904

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 14

ER -