Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes

Wei Li; Wei Yuan; Min Shi; Erik Hernandez; Guigen Li

doi:10.1021/ol902505p

Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes

Wei Li, Wei Yuan, Min Shi, Erik Hernandez, Guigen Li

Chemistry and Biochemistry

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

38 Scopus citations

Abstract

"Chemical Equation Presented" An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)₂]₂ as the catalyst in co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)₂]₂ and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

Original language	English
Pages (from-to)	64-67
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	1
DOIs	https://doi.org/10.1021/ol902505p
State	Published - Jan 1 2010

Access to Document

10.1021/ol902505p

Cite this

@article{3777fe43c6cc40548d639fbebf7934c9,

title = "Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes",

abstract = "{"}Chemical Equation Presented{"} An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)2]2 as the catalyst in co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)2]2 and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.",

author = "Wei Li and Wei Yuan and Min Shi and Erik Hernandez and Guigen Li",

year = "2010",

month = jan,

day = "1",

doi = "10.1021/ol902505p",

language = "English",

volume = "12",

pages = "64--67",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "1",

}

TY - JOUR

T1 - Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes

AU - Li, Wei

AU - Yuan, Wei

AU - Shi, Min

AU - Hernandez, Erik

AU - Li, Guigen

PY - 2010/1/1

Y1 - 2010/1/1

N2 - "Chemical Equation Presented" An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)2]2 as the catalyst in co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)2]2 and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

AB - "Chemical Equation Presented" An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)2]2 as the catalyst in co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)2]2 and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

UR - http://www.scopus.com/inward/record.url?scp=73949110562&partnerID=8YFLogxK

U2 - 10.1021/ol902505p

DO - 10.1021/ol902505p

M3 - Article

C2 - 19950891

AN - SCOPUS:73949110562

VL - 12

SP - 64

EP - 67

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -

Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this