An Exceptionally Mild Catalytic Thioester Aldol Reaction Inspired by Polyketide Biosynthesis
- 14 February 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (10) , 2852-2853
- https://doi.org/10.1021/ja029452x
Abstract
This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords β-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be performed under exceptionally mild conditions (23 °C, open to the air, wet solvent). Methyl malonic acid half thioesters afforded syn aldol products with distereoselectivities greater than 6:1.Keywords
This publication has 16 references indexed in Scilit:
- A New Protocol for a Regioselective Aldol Condensation as an Alternative Convenient Synthesis of β-Ketols and α,β-Unsaturated KetonesThe Journal of Organic Chemistry, 2002
- Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?Molecules, 2001
- A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst DesignJournal of the American Chemical Society, 2000
- The Knoevenagel Reactions of Aldehydes with Carboxy Compounds. I. Reactions of p-Nitrobenzaldehyde with Active Methine CompoundsBulletin of the Chemical Society of Japan, 1988
- Why Nature Chose PhosphatesScience, 1987
- Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complexJournal of the American Chemical Society, 1986
- A Convenient Method for the Preparation of S-Esters of Thio Analogs of Malonic AcidBulletin of the Chemical Society of Japan, 1982
- C‐Acylation under Virtually Neutral ConditionsAngewandte Chemie International Edition in English, 1979
- Acetyl transfer reaction in catechol acetate malonate. Model for the biosynthesis of polyketides and fatty acidsJournal of the American Chemical Society, 1975
- A NEW SYNTHETIC METHOD FOR THE PREPARATION OF α-SUBSTITUTED β-KETOESTERSJournal of the American Chemical Society, 1959