Stereoselective allylation of chiral monoperoxyacetals

Aqeel Ahmed; Patrick H. Dussault

doi:10.1016/j.tet.2005.02.071

Stereoselective allylation of chiral monoperoxyacetals

Aqeel Ahmed, Patrick H. Dussault

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

18 Scopus citations

Abstract

Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.

Original language	English (US)
Pages (from-to)	4657-4670
Number of pages	14
Journal	Tetrahedron
Volume	61
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2005.02.071
State	Published - May 9 2005

Keywords

Allylation
Lewis acid
Monoperoxyacetal
Neighbouring group
Peroxide
Stereoinduction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.02.071

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title = "Stereoselective allylation of chiral monoperoxyacetals",

abstract = "Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.",

keywords = "Allylation, Lewis acid, Monoperoxyacetal, Neighbouring group, Peroxide, Stereoinduction",

author = "Aqeel Ahmed and Dussault, {Patrick H.}",

note = "Funding Information: We thank the NIH for financial support and Dr. Dipanjan Nag for assistance with NMR experiments. NMR spectra were recorded on equipment purchased with NSF support (MRI 0079750 and CHE 0091975).",

year = "2005",

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doi = "10.1016/j.tet.2005.02.071",

language = "English (US)",

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TY - JOUR

T1 - Stereoselective allylation of chiral monoperoxyacetals

AU - Ahmed, Aqeel

AU - Dussault, Patrick H.

N1 - Funding Information: We thank the NIH for financial support and Dr. Dipanjan Nag for assistance with NMR experiments. NMR spectra were recorded on equipment purchased with NSF support (MRI 0079750 and CHE 0091975).

PY - 2005/5/9

Y1 - 2005/5/9

N2 - Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.

AB - Neighboring iodo-, alkoxy-, acetoxy- and silyl groups impart useful levels of diastereoselection in the Lewis acid-mediated allylation of monoperoxyacetals. Although monoperoxyacetals are found to be considerably less reactive than corresponding nonperoxidic acetals, similar stereochemical trends are observed in the two series.

KW - Allylation

KW - Lewis acid

KW - Monoperoxyacetal

KW - Neighbouring group

KW - Peroxide

KW - Stereoinduction

UR - http://www.scopus.com/inward/record.url?scp=17144408271&partnerID=8YFLogxK

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U2 - 10.1016/j.tet.2005.02.071

DO - 10.1016/j.tet.2005.02.071

M3 - Article

AN - SCOPUS:17144408271

SN - 0040-4020

VL - 61

SP - 4657

EP - 4670

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Stereoselective allylation of chiral monoperoxyacetals

Abstract

Keywords

ASJC Scopus subject areas

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