Unusual Reagent Control of Diastereoselectivity in the 1,2-Addition of Hard Carbon Nucleophiles to C6-Heteroatom Substituted Cyclohexenones
Authors:
- 16 November 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (25) , 4007-4010
Abstract
A surprising and synthetically useful counterion-dependent reversal of diastereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C6-heterosubstituted cyclohexenones. In general, Grignard reagents added syn to the C6-substituent and Li reagents added anti, although some exceptions were found. Selectivities could be increased in some cases by appropriate choice of solvent and/or cosolvent.Keywords
This publication has 18 references indexed in Scilit:
- Comparison of the magnetic anisotropy of the cyclopropane and cyclobutane ring systems as probed by proton NMR spectroscopy of spiro[cycloalkanefluorenes]The Journal of Organic Chemistry, 1991
- Tandem cycloaddition/radical cyclization, a widely applicable strategy for the rapid assembly of polycyclic systemsThe Journal of Organic Chemistry, 1988
- The crystal structures of two cesides show that cesium(1-) is the largest monotomic ionJournal of the American Chemical Society, 1987
- Synthesis and structure of a diiron divinylidene complex formed by oxidative carbon-carbon couplingJournal of the American Chemical Society, 1987
- [6 + 3] Cycloaddition to nine-membered ring carbocyclesJournal of the American Chemical Society, 1987
- Macroexpansion methodology. 3. Eight-step synthesis of (-)-(3Z)-cembrene AJournal of the American Chemical Society, 1985
- Preparation of an aromatic synthon for maytansinoid synthesisThe Journal of Organic Chemistry, 1985
- Stereoselective conversion of keto groups into methyl vinyl quaternary carbon centersJournal of the American Chemical Society, 1978
- Resonance Raman study of oxyhemocyanin with unsymmetrically labeled oxygenJournal of the American Chemical Society, 1977
- Stereochemistry of organometallic compound addition to ketonesChemical Reviews, 1975