A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols

Yeong Jiunn Jang; Jhenyi Wu; Yung Feng Lin; Ching Fa Yao

doi:10.1016/j.tet.2004.06.001

A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols

Yeong Jiunn Jang, Jhenyi Wu, Yung Feng Lin, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

10 Citations (Scopus)

Abstract

A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed.

Original language	English
Pages (from-to)	6565-6574
Number of pages	10
Journal	Tetrahedron
Volume	60
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2004.06.001
Publication status	Published - 2004 Jul 26

Keywords

(E)-β-Nitrostyrene
Diastereoselective
Homoallylic alcohol
Radical

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2004.06.001

Cite this

@article{729c212bc0774dab8f360b573bda6b85,

title = "A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols",

abstract = "A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed.",

keywords = "(E)-β-Nitrostyrene, Diastereoselective, Homoallylic alcohol, Radical",

author = "Jang, {Yeong Jiunn} and Jhenyi Wu and Lin, {Yung Feng} and Yao, {Ching Fa}",

note = "Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.",

year = "2004",

month = jul,

day = "26",

doi = "10.1016/j.tet.2004.06.001",

language = "English",

volume = "60",

pages = "6565--6574",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "31",

}

TY - JOUR

T1 - A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols

AU - Jang, Yeong Jiunn

AU - Wu, Jhenyi

AU - Lin, Yung Feng

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.

PY - 2004/7/26

Y1 - 2004/7/26

N2 - A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed.

AB - A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed.

KW - (E)-β-Nitrostyrene

KW - Diastereoselective

KW - Homoallylic alcohol

KW - Radical

UR - http://www.scopus.com/inward/record.url?scp=4143128102&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4143128102&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.06.001

DO - 10.1016/j.tet.2004.06.001

M3 - Article

AN - SCOPUS:4143128102

SN - 0040-4020

VL - 60

SP - 6565

EP - 6574

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this