Method for the synthesis of chiral allylic alcohols utilizing selone based chiral derivatizing agents
Abstract
Molecules containing a chiral 1,2-diol unit are synthesized from reactions between aldehydes and N-acyl selones. A chilled N-acyl selone is reacted with a Lewis acid such as TiCl.sub.4 and mixed with a tertiary amine such as diisopropylethylamine to generate an enolate solution. Upon further chilling of the enolate solution a desired aldehyde is added and after an acceptable reaction period a quencher is introduced and the product isolated.
- Inventors:
-
- (White Rock, NM)
- Issue Date:
- Research Org.:
- Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
- OSTI Identifier:
- 874719
- Patent Number(s):
- 6448409
- Assignee:
- The Regents of the University of California (Oakland, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- W-7405-ENG-36
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- method; synthesis; chiral; allylic; alcohols; utilizing; selone; based; derivatizing; agents; molecules; containing; 12-diol; unit; synthesized; reactions; aldehydes; n-acyl; selones; chilled; reacted; lewis; acid; ticlsub4; mixed; tertiary; amine; diisopropylethylamine; generate; enolate; solution; chilling; aldehyde; added; acceptable; reaction; period; quencher; introduced; product; isolated; tertiary amine; /999/
Citation Formats
Silks, III, Louis A. Method for the synthesis of chiral allylic alcohols utilizing selone based chiral derivatizing agents. United States: N. p., 2002.
Web.
Silks, III, Louis A. Method for the synthesis of chiral allylic alcohols utilizing selone based chiral derivatizing agents. United States.
Silks, III, Louis A. Tue .
"Method for the synthesis of chiral allylic alcohols utilizing selone based chiral derivatizing agents". United States. https://www.osti.gov/servlets/purl/874719.
@article{osti_874719,
title = {Method for the synthesis of chiral allylic alcohols utilizing selone based chiral derivatizing agents},
author = {Silks, III, Louis A.},
abstractNote = {Molecules containing a chiral 1,2-diol unit are synthesized from reactions between aldehydes and N-acyl selones. A chilled N-acyl selone is reacted with a Lewis acid such as TiCl.sub.4 and mixed with a tertiary amine such as diisopropylethylamine to generate an enolate solution. Upon further chilling of the enolate solution a desired aldehyde is added and after an acceptable reaction period a quencher is introduced and the product isolated.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2002},
month = {1}
}
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.