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^*

^*Corresponding author for this work

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

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 language	English
Pages (from-to)	8956-8958
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	25
DOIs	https://doi.org/10.1021/jo049203m
Publication status	Published - 2004 Dec 10
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo049203m

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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",

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journal = "Journal of Organic Chemistry",

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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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

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

Abstract

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