Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde

Hang Xu; Sardaraz Khan; Hongfang Li; Xue Wu; Yong Jian Zhang

doi:10.1021/acs.orglett.8b03665

Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde

Hang Xu, Sardaraz Khan, Hongfang Li, Xue Wu, Yong Jian Zhang^*

^*Corresponding author for this work

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

47 Scopus citations

Abstract

An efficient method for the enantioselective construction of tertiary 1,3-diols via Pd-catalyzed asymmetric allylic cycloaddition of vinyloxetanes with an abundant feedstock, formaldehyde, is developed. Using the palladium complex generated in situ from Pd ₂ (dba) ₃ ·CHCl ₃ and phosphoramidite L3 as a catalyst under mild conditions, the process allows one to convert racemic 2-substituted 2-vinyloxetanes (1) to the corresponding 1,3-dioxanes (2) as methylene acetal protected tertiary 1,3-diols in high yields with good to excellent enantioselectivities.

Original language	English
Pages (from-to)	214-217
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.8b03665
State	Published - 4 Jan 2019
Externally published	Yes

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Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde",

abstract = " An efficient method for the enantioselective construction of tertiary 1,3-diols via Pd-catalyzed asymmetric allylic cycloaddition of vinyloxetanes with an abundant feedstock, formaldehyde, is developed. Using the palladium complex generated in situ from Pd 2 (dba) 3 ·CHCl 3 and phosphoramidite L3 as a catalyst under mild conditions, the process allows one to convert racemic 2-substituted 2-vinyloxetanes (1) to the corresponding 1,3-dioxanes (2) as methylene acetal protected tertiary 1,3-diols in high yields with good to excellent enantioselectivities.",

author = "Hang Xu and Sardaraz Khan and Hongfang Li and Xue Wu and Zhang, \{Yong Jian\}",

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year = "2019",

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doi = "10.1021/acs.orglett.8b03665",

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AU - Khan, Sardaraz

AU - Li, Hongfang

AU - Wu, Xue

AU - Zhang, Yong Jian

PY - 2019/1/4

Y1 - 2019/1/4

N2 - An efficient method for the enantioselective construction of tertiary 1,3-diols via Pd-catalyzed asymmetric allylic cycloaddition of vinyloxetanes with an abundant feedstock, formaldehyde, is developed. Using the palladium complex generated in situ from Pd 2 (dba) 3 ·CHCl 3 and phosphoramidite L3 as a catalyst under mild conditions, the process allows one to convert racemic 2-substituted 2-vinyloxetanes (1) to the corresponding 1,3-dioxanes (2) as methylene acetal protected tertiary 1,3-diols in high yields with good to excellent enantioselectivities.

AB - An efficient method for the enantioselective construction of tertiary 1,3-diols via Pd-catalyzed asymmetric allylic cycloaddition of vinyloxetanes with an abundant feedstock, formaldehyde, is developed. Using the palladium complex generated in situ from Pd 2 (dba) 3 ·CHCl 3 and phosphoramidite L3 as a catalyst under mild conditions, the process allows one to convert racemic 2-substituted 2-vinyloxetanes (1) to the corresponding 1,3-dioxanes (2) as methylene acetal protected tertiary 1,3-diols in high yields with good to excellent enantioselectivities.

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JF - Organic Letters

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ER -

Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyloxetanes with Formaldehyde

Abstract

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