Catalytic Asymmetric Propionate Aldol Reactions via Acyl Halide−Aldehyde Cyclocondensations
- 1 June 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (13), 1883-1886
- https://doi.org/10.1021/ol005968e
Abstract
Catalyzed asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions afford highly enantiomerically enriched 3,4-disubstituted-2-oxetanones. These reactions constitute catalytic asymmetric propionate aldol additions. An optically active Al(III)-triamine complex (10 mol %) catalyzes the di(isopropyl)ethylamine-mediated cyclocondensation of propionyl bromide and a variety of aldehydes to afford beta-lactone adducts with uniformly high enantioselection (90 --> 98% ee), diastereoselection (74 --> 98% de), and chemical yields (78-90%). Lactone ring opening reveals that the enantiomerically enriched beta-lactones act as surrogates for syn propionate aldol adducts.Keywords
This publication has 3 references indexed in Scilit:
- Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensations. A Strategy for Enantioselective Catalyzed Cross Aldol ReactionsJournal of the American Chemical Society, 1999
- A theoretical study on the mechanism of the thermal and the acid-catalyzed decarboxylation of 2-oxetanones (.beta.-lactones)The Journal of Organic Chemistry, 1989
- Total synthesis of (+)-actinobolinJournal of the American Chemical Society, 1985