Samarium diiodide-promoted intramolecular radical cyclization of (η4-diene)Fe(CO)3 complexes bearing keto side chains

Ming Chang P. Yeh; Fu Chun Wang; Jin Juean Tu; Sun Chi Chang; Cheng Chiang Chou; Jin Wei Liao

doi:10.1021/om980663d

Samarium diiodide-promoted intramolecular radical cyclization of (η⁴-diene)Fe(CO)₃ complexes bearing keto side chains

Ming Chang P. Yeh^*, Fu Chun Wang, Jin Juean Tu, Sun Chi Chang, Cheng Chiang Chou, Jin Wei Liao

^*Corresponding author for this work

Department of Chemistry

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

14 Citations (Scopus)

Abstract

Reaction of samarium diiodide with (η⁴-cyclohexadiene)Fe(CO)₃ complexes bearing keto side chains in THF/HMPA/t-BuOH gives fused bicyclo[4.3.0]nonenol derivatives, whereas (η⁴-cycloheptadiene)Fe(CO)₃ analogues produce a bicyclo[5.3.0]decenol ring skeleton. The iron-mediated intramolecular radical addition allows for the direct stereocontrol of three contiguous stereogenic centers of these fused bicyclic skeletons. Under the same reaction conditions, intramolecular ketyl radical cyclization of acyclic (η⁴-1,3-butadiene)Fe(CO)₃ complexes with keto side chains at the terminal position of the diene ligands furnishes disubstituted cyclopentanol and cyclohexanol derivatives with excellent diastereoselectivity.

Original language	English
Pages (from-to)	5656-5662
Number of pages	7
Journal	Organometallics
Volume	17
Issue number	26
DOIs	https://doi.org/10.1021/om980663d
Publication status	Published - 1998

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1021/om980663d

Cite this

@article{7075672580284a6ab2100001a732c42f,

title = "Samarium diiodide-promoted intramolecular radical cyclization of (η4-diene)Fe(CO)3 complexes bearing keto side chains",

abstract = "Reaction of samarium diiodide with (η4-cyclohexadiene)Fe(CO)3 complexes bearing keto side chains in THF/HMPA/t-BuOH gives fused bicyclo[4.3.0]nonenol derivatives, whereas (η4-cycloheptadiene)Fe(CO)3 analogues produce a bicyclo[5.3.0]decenol ring skeleton. The iron-mediated intramolecular radical addition allows for the direct stereocontrol of three contiguous stereogenic centers of these fused bicyclic skeletons. Under the same reaction conditions, intramolecular ketyl radical cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with keto side chains at the terminal position of the diene ligands furnishes disubstituted cyclopentanol and cyclohexanol derivatives with excellent diastereoselectivity.",

author = "Yeh, {Ming Chang P.} and Wang, {Fu Chun} and Tu, {Jin Juean} and Chang, {Sun Chi} and Chou, {Cheng Chiang} and Liao, {Jin Wei}",

year = "1998",

doi = "10.1021/om980663d",

language = "English",

volume = "17",

pages = "5656--5662",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Samarium diiodide-promoted intramolecular radical cyclization of (η4-diene)Fe(CO)3 complexes bearing keto side chains

AU - Yeh, Ming Chang P.

AU - Wang, Fu Chun

AU - Tu, Jin Juean

AU - Chang, Sun Chi

AU - Chou, Cheng Chiang

AU - Liao, Jin Wei

PY - 1998

Y1 - 1998

N2 - Reaction of samarium diiodide with (η4-cyclohexadiene)Fe(CO)3 complexes bearing keto side chains in THF/HMPA/t-BuOH gives fused bicyclo[4.3.0]nonenol derivatives, whereas (η4-cycloheptadiene)Fe(CO)3 analogues produce a bicyclo[5.3.0]decenol ring skeleton. The iron-mediated intramolecular radical addition allows for the direct stereocontrol of three contiguous stereogenic centers of these fused bicyclic skeletons. Under the same reaction conditions, intramolecular ketyl radical cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with keto side chains at the terminal position of the diene ligands furnishes disubstituted cyclopentanol and cyclohexanol derivatives with excellent diastereoselectivity.

AB - Reaction of samarium diiodide with (η4-cyclohexadiene)Fe(CO)3 complexes bearing keto side chains in THF/HMPA/t-BuOH gives fused bicyclo[4.3.0]nonenol derivatives, whereas (η4-cycloheptadiene)Fe(CO)3 analogues produce a bicyclo[5.3.0]decenol ring skeleton. The iron-mediated intramolecular radical addition allows for the direct stereocontrol of three contiguous stereogenic centers of these fused bicyclic skeletons. Under the same reaction conditions, intramolecular ketyl radical cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with keto side chains at the terminal position of the diene ligands furnishes disubstituted cyclopentanol and cyclohexanol derivatives with excellent diastereoselectivity.

UR - http://www.scopus.com/inward/record.url?scp=0001017256&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001017256&partnerID=8YFLogxK

U2 - 10.1021/om980663d

DO - 10.1021/om980663d

M3 - Article

AN - SCOPUS:0001017256

SN - 0276-7333

VL - 17

SP - 5656

EP - 5662

JO - Organometallics

JF - Organometallics

IS - 26

ER -

Samarium diiodide-promoted intramolecular radical cyclization of (η⁴-diene)Fe(CO)₃ complexes bearing keto side chains

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this