Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

Mitsuru Shindo; Tomoyuki Sugioka; Kozo Shishido

doi:10.1016/j.tetlet.2004.10.049

Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

Mitsuru Shindo, Tomoyuki Sugioka, Kozo Shishido

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

15 Citations (Scopus)

Abstract

The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF ₃ mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO ₄ mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.

Original language	English
Pages (from-to)	9265-9268
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.049
Publication status	Published - Dec 6 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.10.049

Cite this

@article{2fb9ea33ce9f4ff18cc064a5a6bdb87f,

title = "Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides",

abstract = "The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO 4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.",

author = "Mitsuru Shindo and Tomoyuki Sugioka and Kozo Shishido",

note = "Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan.",

year = "2004",

month = dec,

day = "6",

doi = "10.1016/j.tetlet.2004.10.049",

language = "English",

volume = "45",

pages = "9265--9268",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "50",

}

TY - JOUR

T1 - Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

AU - Shindo, Mitsuru

AU - Sugioka, Tomoyuki

AU - Shishido, Kozo

N1 - Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan.

PY - 2004/12/6

Y1 - 2004/12/6

N2 - The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO 4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.

AB - The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO 4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively.

UR - http://www.scopus.com/inward/record.url?scp=8544222635&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=8544222635&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.10.049

DO - 10.1016/j.tetlet.2004.10.049

M3 - Article

AN - SCOPUS:8544222635

SN - 0040-4039

VL - 45

SP - 9265

EP - 9268

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this