Highly Diastereoselective Synthesis of Propargylic 1,2-anti-Diol Derivatives Using α-Alkoxypropargylstannanes
- 28 August 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (19) , 3057-3060
- https://doi.org/10.1021/ol016536m
Abstract
Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha-alkoxypropargylstannanes 4a and 4b to aldehydes in the presence of BuSnCl(3). We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions. Reaction: see text.Keywords
This publication has 24 references indexed in Scilit:
- Comparative Studies on the Synthesis of an anti,syn Stereotriad with Chiral Allenylstannane and Allenylindium ReagentsThe Journal of Organic Chemistry, 1997
- Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric SynthesisChemical Reviews, 1996
- A Practical Method for the Removal of Organotin Residues from Reaction MixturesThe Journal of Organic Chemistry, 1996
- Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric ReagentsThe Journal of Organic Chemistry, 1995
- Propargyl and Allenyl OrganometallicsPublished by Elsevier ,1991
- Diastereoselective additions of allenylstannanes to aldehydesThe Journal of Organic Chemistry, 1990
- An Improved Procedure for Cyclisation of Chalcones to Flavanones Using Celite Supported Potassium Fluoride in Methanol: Total Synthesis of BavachininSynthetic Communications, 1990
- Allenic zinc reagents. A remarkably regio- and diastereoselective synthesis of 2-substituted homopropargylic alcoholsThe Journal of Organic Chemistry, 1984
- Propargylic titanium reagents. Regio- and stereocontrolled synthesis of allenic and acetylenic alcoholsThe Journal of Organic Chemistry, 1982
- Recommended Work-up Procedure for Reductions Employing Tri-n-butyltin HydrideSynthesis, 1979