2015
DOI: 10.1002/ange.201501995
|View full text |Cite
|
Sign up to set email alerts
|

Copper‐Catalyzed Oxy‐Alkenylation of Homoallylic Alcohols to Generate Functional syn‐1,3‐Diol Derivatives

Abstract: A novel method for the synthesis of a wide range of functionalized 1,3‐diol derivatives is reported. Employing a copper‐catalyzed oxy‐alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn‐1,3‐carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide‐like fragments.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
1
0

Year Published

2015
2015
2023
2023

Publication Types

Select...
6

Relationship

0
6

Authors

Journals

citations
Cited by 21 publications
(1 citation statement)
references
References 85 publications
0
1
0
Order By: Relevance
“…Plenty of methods for the stereoselective synthesis of 1,3-diols have been developed: Allylation of β-hydroxyaldehydes, catalytic aldol reactions, stereoselective reduction, stereoselective hydrogenation, catalytic olefin carbonylation, biocatalytic methods, cyclization of homoallylic carbonates, Michael addition, tandem hemiacetal formation/Tsuji–Trost reation, catalytic oxy-alkenylation of homoallylic alcohols, or catalytic dehydrative allylation just to mention a few. We herein report a diastereoselective palladium-catalyzed intramolecular cyclization of in situ formed allenyl hemiacetals in order to access syn -configured methylene acetal protected 1,3-diols selectively.…”
mentioning
confidence: 99%
“…Plenty of methods for the stereoselective synthesis of 1,3-diols have been developed: Allylation of β-hydroxyaldehydes, catalytic aldol reactions, stereoselective reduction, stereoselective hydrogenation, catalytic olefin carbonylation, biocatalytic methods, cyclization of homoallylic carbonates, Michael addition, tandem hemiacetal formation/Tsuji–Trost reation, catalytic oxy-alkenylation of homoallylic alcohols, or catalytic dehydrative allylation just to mention a few. We herein report a diastereoselective palladium-catalyzed intramolecular cyclization of in situ formed allenyl hemiacetals in order to access syn -configured methylene acetal protected 1,3-diols selectively.…”
mentioning
confidence: 99%