Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement

Kenji Matsumoto; Naoyuki Mizushina; Masahiro Yoshida; Mitsuru Shindo

doi:10.1055/s-0036-1590970

Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement

Kenji Matsumoto, Naoyuki Mizushina, Masahiro Yoshida, Mitsuru Shindo

物質基盤化学部門

研究成果: Contribution to journal › Article › 査読

4 被引用数 (Scopus)

抄録

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.

本文言語	英語
論文番号	st-2017-u0300-l
ページ（範囲）	2340-2344
ページ数	5
ジャーナル	Synlett
巻	28
号	17
DOI	https://doi.org/10.1055/s-0036-1590970
出版ステータス	出版済み - 10 23 2017

All Science Journal Classification (ASJC) codes

Organic Chemistry

文献へのアクセス

10.1055/s-0036-1590970

フィンガープリント「Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{97adf65cd686421eb3dd8016c2748c87,

title = "Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement",

abstract = "We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.",

author = "Kenji Matsumoto and Naoyuki Mizushina and Masahiro Yoshida and Mitsuru Shindo",

year = "2017",

month = oct,

day = "23",

doi = "10.1055/s-0036-1590970",

language = "English",

volume = "28",

pages = "2340--2344",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "17",

}

TY - JOUR

T1 - Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene-Claisen Rearrangement

AU - Matsumoto, Kenji

AU - Mizushina, Naoyuki

AU - Yoshida, Masahiro

AU - Shindo, Mitsuru

PY - 2017/10/23

Y1 - 2017/10/23

N2 - We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.

AB - We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene-Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E,3 Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels-Alder reactions are described.

UR - http://www.scopus.com/inward/record.url?scp=85026557493&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85026557493&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1590970

DO - 10.1055/s-0036-1590970

M3 - Article

AN - SCOPUS:85026557493

VL - 28

SP - 2340

EP - 2344

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 17

M1 - st-2017-u0300-l

ER -