Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: A cationic cascade cyclization

Bin Li; Yu Jun Zhao; Yin Chang Lai; Teck Peng Loh

doi:10.1002/anie.201202699

Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: A cationic cascade cyclization

Bin Li, Yu Jun Zhao, Yin Chang Lai, Teck Peng Loh^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used.

Original language	English
Pages (from-to)	8041-8045
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	32
DOIs	https://doi.org/10.1002/anie.201202699
Publication status	Published - Aug 6 2012
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

aldol reaction
cyclization
heterocycles
synthetic methods
titanium

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10.1002/anie.201202699

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abstract = "High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used.",

keywords = "aldol reaction, cyclization, heterocycles, synthetic methods, titanium",

author = "Bin Li and Zhao, {Yu Jun} and Lai, {Yin Chang} and Loh, {Teck Peng}",

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T1 - Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes

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AU - Li, Bin

AU - Zhao, Yu Jun

AU - Lai, Yin Chang

AU - Loh, Teck Peng

PY - 2012/8/6

Y1 - 2012/8/6

N2 - High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used.

AB - High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used.

KW - aldol reaction

KW - cyclization

KW - heterocycles

KW - synthetic methods

KW - titanium

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ER -

Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: A cationic cascade cyclization

Abstract

ASJC Scopus Subject Areas

Keywords

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