An unusual intramolecular acetal alkylation

Xiuchun Gao; Punit P. Seth; John K. Bitok; Nancy I. Totah

doi:10.1055/s-2005-863748

An unusual intramolecular acetal alkylation

Xiuchun Gao, Punit P. Seth, John K. Bitok, Nancy I. Totah

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

2 Scopus citations

Abstract

Upon treatment with Grignard reagents, suitably functionalized cis-fused bicyclic ketone acetals undergo intramolecular acetal alkylation to provide oxabicyclo[3.3.1]nonane derivatives. This transformation results in the formation of up to three stereogenic centers with high levels of stereoselectivity. Product distribution and stereochemistry vary with substrate substitution and the Grignard reagent utilized.

Original language	English (US)
Pages (from-to)	819-823
Number of pages	5
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-2005-863748
State	Published - Mar 21 2005

Keywords

Acetals
Alkylation
Annulation
Grignard reagents
Stereoselectivity

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2005-863748

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title = "An unusual intramolecular acetal alkylation",

abstract = "Upon treatment with Grignard reagents, suitably functionalized cis-fused bicyclic ketone acetals undergo intramolecular acetal alkylation to provide oxabicyclo[3.3.1]nonane derivatives. This transformation results in the formation of up to three stereogenic centers with high levels of stereoselectivity. Product distribution and stereochemistry vary with substrate substitution and the Grignard reagent utilized.",

keywords = "Acetals, Alkylation, Annulation, Grignard reagents, Stereoselectivity",

author = "Xiuchun Gao and Seth, {Punit P.} and Bitok, {John K.} and Totah, {Nancy I.}",

year = "2005",

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language = "English (US)",

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T1 - An unusual intramolecular acetal alkylation

AU - Gao, Xiuchun

AU - Seth, Punit P.

AU - Bitok, John K.

AU - Totah, Nancy I.

PY - 2005/3/21

Y1 - 2005/3/21

N2 - Upon treatment with Grignard reagents, suitably functionalized cis-fused bicyclic ketone acetals undergo intramolecular acetal alkylation to provide oxabicyclo[3.3.1]nonane derivatives. This transformation results in the formation of up to three stereogenic centers with high levels of stereoselectivity. Product distribution and stereochemistry vary with substrate substitution and the Grignard reagent utilized.

AB - Upon treatment with Grignard reagents, suitably functionalized cis-fused bicyclic ketone acetals undergo intramolecular acetal alkylation to provide oxabicyclo[3.3.1]nonane derivatives. This transformation results in the formation of up to three stereogenic centers with high levels of stereoselectivity. Product distribution and stereochemistry vary with substrate substitution and the Grignard reagent utilized.

KW - Acetals

KW - Alkylation

KW - Annulation

KW - Grignard reagents

KW - Stereoselectivity

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JO - Synlett

JF - Synlett

IS - 5

ER -

An unusual intramolecular acetal alkylation

Abstract

Keywords

ASJC Scopus subject areas

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