Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia cope rearrangement

Teck Peng Loh; Qi Ying Hu; Li Ting Ma

doi:10.1021/ol026136e

Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia cope rearrangement

Teck Peng Loh^*, Qi Ying Hu, Li Ting Ma

^*Corresponding author for this work

National University of Singapore

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

33 Citations (Scopus)

Abstract

(Matrix presented) Poor stereoselectivity caused by the involvement of side reaction pathways was observed in the In(OTf)₃-catalyzed allyl-transfer reaction (R = electron-withdrawing group). Subsequently, it was found that the employment of triflic acid (TFA) as catalyst could successfully suppress the side reaction pathways and, hence, achieve high stereoselectivity.

Original language	English
Pages (from-to)	2389-2391
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	14
DOIs	https://doi.org/10.1021/ol026136e
Publication status	Published - Jul 11 2002
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol026136e

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title = "Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia cope rearrangement",

abstract = "(Matrix presented) Poor stereoselectivity caused by the involvement of side reaction pathways was observed in the In(OTf)3-catalyzed allyl-transfer reaction (R = electron-withdrawing group). Subsequently, it was found that the employment of triflic acid (TFA) as catalyst could successfully suppress the side reaction pathways and, hence, achieve high stereoselectivity.",

author = "Loh, {Teck Peng} and Hu, {Qi Ying} and Ma, {Li Ting}",

year = "2002",

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T1 - Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia cope rearrangement

AU - Loh, Teck Peng

AU - Hu, Qi Ying

AU - Ma, Li Ting

PY - 2002/7/11

Y1 - 2002/7/11

N2 - (Matrix presented) Poor stereoselectivity caused by the involvement of side reaction pathways was observed in the In(OTf)3-catalyzed allyl-transfer reaction (R = electron-withdrawing group). Subsequently, it was found that the employment of triflic acid (TFA) as catalyst could successfully suppress the side reaction pathways and, hence, achieve high stereoselectivity.

AB - (Matrix presented) Poor stereoselectivity caused by the involvement of side reaction pathways was observed in the In(OTf)3-catalyzed allyl-transfer reaction (R = electron-withdrawing group). Subsequently, it was found that the employment of triflic acid (TFA) as catalyst could successfully suppress the side reaction pathways and, hence, achieve high stereoselectivity.

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Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia cope rearrangement

Abstract

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