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

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8956-8958
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number25
DOIs
Publication statusPublished - 2004 Dec 10
Externally publishedYes

Fingerprint

Cyclization
Ketones
Alkenes
Aldehydes
Acetates
Alcohols

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Acetoxyl group directed cyclization promoted by SmI2 : Directing group determined stereocomplementarity. / Kan, Toshiyuki; Hosokawa, Seijiro; Nara, Shinji; Tamiya, Hiroaki; Shirahama, Haruhisa; Matsuda, Fuyuhiko.

In: Journal of Organic Chemistry, Vol. 69, No. 25, 10.12.2004, p. 8956-8958.

Research output: Contribution to journalArticle

Kan, Toshiyuki ; Hosokawa, Seijiro ; Nara, Shinji ; Tamiya, Hiroaki ; Shirahama, Haruhisa ; Matsuda, Fuyuhiko. / Acetoxyl group directed cyclization promoted by SmI2 : Directing group determined stereocomplementarity. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 25. pp. 8956-8958.
@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 = "12",
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

VL - 69

SP - 8956

EP - 8958

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 25

ER -