One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents

Natsuko Kagawa; Antoinette E Nibbs; Viresh H Rawal

doi:10.1021/acs.orglett.6b00790

One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents

Org Lett. 2016 May 20;18(10):2363-6. doi: 10.1021/acs.orglett.6b00790. Epub 2016 May 2.

Authors

Natsuko Kagawa^{1

2}, Antoinette E Nibbs³, Viresh H Rawal³

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chiba 260-8675, Japan.
² Center for Environment, Health and Field Sciences, Chiba University , 6-2-1 Kashiwa-no-ha, Kashiwa 277-0882, Japan.
³ Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.

PMID: 27135854
DOI: 10.1021/acs.orglett.6b00790

Abstract

A method is reported for the one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide. The process involves the Mitsunobu reaction with an alkoxymalononitrile, followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Amides / chemical synthesis*
Amides / chemistry
Carbon / chemistry*
Carboxylic Acids / chemical synthesis*
Carboxylic Acids / chemistry
Chemistry Techniques, Synthetic / methods*
Esters / chemical synthesis*
Esters / chemistry
Indicators and Reagents / chemistry
Molecular Structure
Stereoisomerism

Substances

Alcohols
Amides
Carboxylic Acids
Esters
Indicators and Reagents
Carbon

Grants and funding

R01 GM069990/GM/NIGMS NIH HHS/United States