Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone: A facile synthesis of silyl peroxide and its reactions

Masanori Murakami; Kyohei Sakita; Kazunobu Igawa; Katsuhiko Tomooka

doi:10.1021/ol061635r

Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone: A facile synthesis of silyl peroxide and its reactions

Masanori Murakami
, Kyohei Sakita
, Kazunobu Igawa
, Katsuhiko Tomooka

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

31 Citations (Scopus)

Abstract

A reaction of γ-silyl allylic alcohol and its ether with ozone provides synthetically versatile α-formyl silyl peroxide in good yield without normal fission of carbon-carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.

Original language	English
Pages (from-to)	4023-4026
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	18
DOIs	https://doi.org/10.1021/ol061635r
Publication status	Published - Aug 31 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol061635r

Cite this

@article{fc686f3a11e74895a59873cb376f3dca,

title = "Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone: A facile synthesis of silyl peroxide and its reactions",

abstract = "A reaction of γ-silyl allylic alcohol and its ether with ozone provides synthetically versatile α-formyl silyl peroxide in good yield without normal fission of carbon-carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.",

author = "Masanori Murakami and Kyohei Sakita and Kazunobu Igawa and Katsuhiko Tomooka",

year = "2006",

month = aug,

day = "31",

doi = "10.1021/ol061635r",

language = "English",

volume = "8",

pages = "4023--4026",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone

T2 - A facile synthesis of silyl peroxide and its reactions

AU - Murakami, Masanori

AU - Sakita, Kyohei

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

PY - 2006/8/31

Y1 - 2006/8/31

N2 - A reaction of γ-silyl allylic alcohol and its ether with ozone provides synthetically versatile α-formyl silyl peroxide in good yield without normal fission of carbon-carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.

AB - A reaction of γ-silyl allylic alcohol and its ether with ozone provides synthetically versatile α-formyl silyl peroxide in good yield without normal fission of carbon-carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.

UR - https://www.scopus.com/pages/publications/33748937863

UR - https://www.scopus.com/pages/publications/33748937863#tab=citedBy

U2 - 10.1021/ol061635r

DO - 10.1021/ol061635r

M3 - Article

C2 - 16928064

AN - SCOPUS:33748937863

SN - 1523-7060

VL - 8

SP - 4023

EP - 4026

JO - Organic letters

JF - Organic letters

IS - 18

ER -

Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone: A facile synthesis of silyl peroxide and its reactions

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this