LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

Wan Shin Kim; Claudio Aquino; Haruki Mizoguchi; Glenn C. Micalizio

doi:10.1016/j.tetlet.2015.01.029

LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

Wan Shin Kim, Claudio Aquino, Haruki Mizoguchi, Glenn C. Micalizio

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

10 Citations (Scopus)

Abstract

Abstract LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.

Original language	English
Article number	45698
Pages (from-to)	3557-3559
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.029
Publication status	Published - May 25 2015
Externally published	Yes

Keywords

Cascade reaction
Hydrindanes
Metallacycle-mediated cross-coupling
Oxidation
[2+2+2]

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2015.01.029

Cite this

@article{99011416fc0a4bfe8bc83714dde61b95,

title = "LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade",

abstract = "Abstract LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.",

keywords = "Cascade reaction, Hydrindanes, Metallacycle-mediated cross-coupling, Oxidation, [2+2+2]",

author = "Kim, {Wan Shin} and Claudio Aquino and Haruki Mizoguchi and Micalizio, {Glenn C.}",

note = "Funding Information: We gratefully acknowledge financial support of this work by the National Institutes of Health-NIGMS ( GM80266 ). Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2015",

month = may,

day = "25",

doi = "10.1016/j.tetlet.2015.01.029",

language = "English",

volume = "56",

pages = "3557--3559",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "23",

}

TY - JOUR

T1 - LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

AU - Kim, Wan Shin

AU - Aquino, Claudio

AU - Mizoguchi, Haruki

AU - Micalizio, Glenn C.

N1 - Funding Information: We gratefully acknowledge financial support of this work by the National Institutes of Health-NIGMS ( GM80266 ). Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - Abstract LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.

AB - Abstract LiOOt-Bu is an effective oxidant for converting the penultimate organometallic intermediate generated in a titanium alkoxide-mediated [2+2+2] reaction cascade to an allylic alcohol. Oxidation of the presumed allylic titanium species is highly regioselective, providing direct access to substituted hydrindanes containing a primary allylic alcohol. In addition to demonstrating the feasibility of this oxidation process, we document the ability to convert the primary allylic alcohol products to angularly substituted cis-fused hydrindanes.

KW - Cascade reaction

KW - Hydrindanes

KW - Metallacycle-mediated cross-coupling

KW - Oxidation

KW - [2+2+2]

UR - http://www.scopus.com/inward/record.url?scp=84939987243&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84939987243&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.01.029

DO - 10.1016/j.tetlet.2015.01.029

M3 - Article

AN - SCOPUS:84939987243

SN - 0040-4039

VL - 56

SP - 3557

EP - 3559

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45698

ER -

LiOOt-Bu as a terminal oxidant in a titanium alkoxide-mediated [2+2+2] reaction cascade

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this