Acetoxyl group directed cyclization promoted by SmI2: Directing group determined stereocomplementarity

Toshiyuki Kan; Seijiro Hosokawa; Shinji Nara; Hiroaki Tamiya; Haruhisa Shirahama; Fuyuhiko Matsuda

doi:10.1021/jo049203m

Acetoxyl group directed cyclization promoted by SmI₂: Directing group determined stereocomplementarity

Toshiyuki Kan, Seijiro Hosokawa, Shinji Nara, Hiroaki Tamiya, Haruhisa Shirahama, Fuyuhiko Matsuda^*

^*この研究の対応する著者

研究成果: Article › 査読

11 被引用数 (Scopus)

抄録

Complete reversal of diastereoselectivity was observed in the SmI ₂-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI₂-induced ketyl-olefin coupling cyclizations of the δ-hydroxy ketone 1 and δ-acetoxy ketone 3.

本文言語	English
ページ（範囲）	8956-8958
ページ数	3
ジャーナル	Journal of Organic Chemistry
巻	69
号	25
DOI	https://doi.org/10.1021/jo049203m
出版ステータス	Published - 2004 12月 10
外部発表	はい

ASJC Scopus subject areas

有機化学

文献へのアクセス

10.1021/jo049203m

他のファイルとリンク

引用スタイル

@article{ccac64d21faf41aeacf6384572e336ec,

title = "Acetoxyl group directed cyclization promoted by SmI2: Directing group determined stereocomplementarity",

abstract = "Complete reversal of diastereoselectivity was observed in the SmI 2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the δ-hydroxy ketone 1 and δ-acetoxy ketone 3.",

author = "Toshiyuki Kan and Seijiro Hosokawa and Shinji Nara and Hiroaki Tamiya and Haruhisa Shirahama and Fuyuhiko Matsuda",

year = "2004",

month = dec,

day = "10",

doi = "10.1021/jo049203m",

language = "English",

volume = "69",

pages = "8956--8958",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - Acetoxyl group directed cyclization promoted by SmI2

T2 - Directing group determined stereocomplementarity

AU - Kan, Toshiyuki

AU - Hosokawa, Seijiro

AU - Nara, Shinji

AU - Tamiya, Hiroaki

AU - Shirahama, Haruhisa

AU - Matsuda, Fuyuhiko

PY - 2004/12/10

Y1 - 2004/12/10

N2 - Complete reversal of diastereoselectivity was observed in the SmI 2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the δ-hydroxy ketone 1 and δ-acetoxy ketone 3.

AB - Complete reversal of diastereoselectivity was observed in the SmI 2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the δ-hydroxy ketone 1 and δ-acetoxy ketone 3.

UR - http://www.scopus.com/inward/record.url?scp=10044230674&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=10044230674&partnerID=8YFLogxK

U2 - 10.1021/jo049203m

DO - 10.1021/jo049203m

M3 - Article

C2 - 15575783

AN - SCOPUS:10044230674

SN - 0022-3263

VL - 69

SP - 8956

EP - 8958

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -