2003•Organic LettersRequires access

Synthesis of Homoallylic Chiral Tertiary Alcohols via Chelation-Controlled Diastereoselective Nucleophilic Addition on α-Alkoxyketones: Application for the Synthesis of the C1−C11Subunit of 8-epi-Fostriecin

P. Veeraraghavan Ramachandran, Haipeng Liu, M. Venkat Ram Reddy, Herbert C. Brown

Abstract

[reaction: see text] Chiral beta-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C(1)-C(11) subunit of C(8)-epi-fostriecin.

About this research paper

What this paper is about

Why it matters

OpenAlex reports 38 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

Key concepts: Chemistry, Stereoselectivity, Chelation, Nucleophilic addition, Tertiary alcohols, Nucleophile, Stereochemistry, BETA (programming language)