Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides

Takahiro Ichige; Daisuke Matsuda; Masaya Nakata

doi:10.1016/j.tetlet.2006.05.023

Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides

Takahiro Ichige, Daisuke Matsuda, Masaya Nakata

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

5 Citations (Scopus)

Abstract

Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively.

Original language	English
Pages (from-to)	4843-4848
Number of pages	6
Journal	Tetrahedron Letters
Volume	47
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.023
Publication status	Published - 2006 Jul 12
Externally published	Yes

Keywords

Anti elimination
Base-promoted ring-opening
Epoxides
Syn elimination
Vinyl iodides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.05.023

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title = "Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides",

abstract = "Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively.",

keywords = "Anti elimination, Base-promoted ring-opening, Epoxides, Syn elimination, Vinyl iodides",

author = "Takahiro Ichige and Daisuke Matsuda and Masaya Nakata",

note = "Funding Information: This research was partially supported by a Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) and a Grant-in-Aid for Scientific Research on Priority Areas 17035076 and 18032067 from MEXT.",

year = "2006",

month = jul,

day = "12",

doi = "10.1016/j.tetlet.2006.05.023",

language = "English",

volume = "47",

pages = "4843--4848",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "28",

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TY - JOUR

T1 - Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides

AU - Ichige, Takahiro

AU - Matsuda, Daisuke

AU - Nakata, Masaya

N1 - Funding Information: This research was partially supported by a Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) and a Grant-in-Aid for Scientific Research on Priority Areas 17035076 and 18032067 from MEXT.

PY - 2006/7/12

Y1 - 2006/7/12

N2 - Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively.

AB - Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively.

KW - Anti elimination

KW - Base-promoted ring-opening

KW - Epoxides

KW - Syn elimination

KW - Vinyl iodides

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DO - 10.1016/j.tetlet.2006.05.023

M3 - Article

AN - SCOPUS:33744811977

VL - 47

SP - 4843

EP - 4848

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 28

ER -

Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides

Abstract

Keywords

ASJC Scopus subject areas

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