Regioselectivity of enamine reactions, preferential 2,2-disubstitution of 2-methylcyclohexanone imines
β Scribed by Peter W. Hickmott; Bruce Rae
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 215 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Secondary enamines, derived from imines of unsyrunetrical a-substituted ketones, react with electrophilic alkenes at the more substituted position to give a,cr-disubstituted ketones on hydrolysis.
Spectroscopic studies"' of imine-enamine tautomerism have shown that, unless the
π SIMILAR VOLUMES
The position isomer (I), having a trisubstituted double bond was originally assigned by Stork and associates to the structure of the pyrrolidine enamine of a substituted cyclohexanone. The tetrasubstituted ethylenic isomer II which was excluded on the basis of N.M.R. spectrum, involves steric interf
## Abstract For Abstract see ChemInform Abstract in Full Text.
Regioselective Nucleophilic Ring Opening Reactions of 2,2-Disubstituted Aziridines -The Asymmetric Synthesis of Ξ±,Ξ±-Disubstituted Amino Acids. -It is shown that, under appropriate conditions, 2,2disubstituted aziridines like (I) and (V) undergo regioselective ring opening reactions at C-3 with carb